CORRECT STR OF Dichlorquinazine

7-chloro-N-[1-[4-[2-[(7-chloroquinolin-4-yl)amino]propyl]piperazin-1-yl]propan-2-yl]quinolin-4-amine;methanesulfonic acid

• 1,4-Piperazinediethanamine, N,N’-bis(7-chloro-4-quinolinyl)-α,α’-dimethyl- (9CI)
• Quinoline, 4,4-[1,4-piperazinediylbis[(1-methylethylene)imino]]bis[7-chloro- (7CI)
• Quinoline, 4,4′-[1,4-piperazinediylbis[(1-methylethylene)imino]]bis[7-chloro- (8CI)
• N¹,N⁴-Bis(7-chloro-4-quinolinyl)-α¹,α⁴-dimethyl-1,4-piperazinediethanamine
• 1,4-Bis[2-(7-chloro-4-quinolylamino)propyl]piperazine

• Bis[(chloro-7”-quinolyl-4”)amino-2′-propyl]-1,4-piperazine
• Dichlorquinazine
• N,N’-Bis(7-chloro-4-quinolyl)-α,α’-dimethylpiperazine-1,4-diethylamine
• NSC 129790
• RP 12278
• WR 3863

WRONG STRUCTURE

WRONG STRUCTURE

Dichlorquinazine

• BRN 0867697
• Dichlorquinazine
• EINECS 234-130-6
• NSC 129790
• RP 12278
• UNII-HT3GAD2SCM
• WR 3863

cas 10547-40-7

C28H32Cl2N6, mw

7-chloro-N-[2-[4-[2-[(7-chloroquinolin-4-yl)amino]propan-2-yl]piperazin-1-yl]propan-2-yl]quinolin-4-amine

VARIANT

RN: 23256-65-7

Molecular Formula, C28-H32-Cl2-N6.C-H4-O3-S, Molecular Weight, 619.6144

• RP-12278 mesylate

• WR-3863 mesylate

• Quinoline, 4,4′-(1,4-piperazinediylbis((1-methylethylene)imino))bis(7-chloro-, tetramethanesulfonate bis((7-chloro-4”-quinolyl)-2′-aminopropyl)-1,4-piperazine methanesulfonate

join me on Linkedin

Anthony Melvin Crasto Ph.D – India | LinkedIn

join me on Researchgate

RESEARCHGATE

join me on Facebook

Anthony Melvin Crasto Dr. | Facebook

• Twitter
• FACEBOOK

join me on twitter

Anthony Melvin Crasto Dr. | twitter

+919321316780 call whatsaapp

EMAIL. amcrasto@amcrasto

/////////////////////////////////////////////////////////////////////////////////////////////////////

PATENTS

BE 626239

4-(Chloro or alkoxy)quinolines are treated with a 1,4-bis(aminoalkyl)piperazine to give the title compds. which can be used as antiinflammatory agents and as amebicides.  Thus, a mixt. of 16.3 g. 4-chloroquinoline, 10 g. 1,4-bis(3-aminopropyl)piperazine, 55 g. PhOH, and 0.2 g. NH₄Cl is heated 5 hrs. at 175°, poured into a mixt. of 500 ml. H₂O and 100 ml. NaOH (d. 1.33), filtered, the ppt. is treated with a mixt. of 80 ml. H₂O and 20 ml. NaOH, the mixt. filtered, and the ppt. washed with 500 ml. H₂O and dried to give 15.9 g. 1,4-bis[3-(4-quinolyl)aminopropyl]piperazine, m. 210°(MeOH-H₂O).  Similarly prepd. are the following I:  n, R, R¹, R², X, Y, m.p.; 2, H, H, H, MeO, H, 245° (HCONMe₂); 2, H, H, H, H, SO₂NMe₂, 271° (HCONMe₂); 2, H, H, H, H, CF₃, 293° (HCONMe₂); 3, Me, H, H, H, H, ∼100°; 3, Me, Ac, H, H, H, -(1); 3, Me, H, H, MeOH, 180° and 190°; 3, Me, Ac, H, MeO, H, -(2); 1, Me, H, Me, H, Cl, 264°; 2, H, H, H, Cl, H, 264° (BuOH); 1, Me, H, H, H, CF₃, 240° (MeCOEt); 2, H, H, H, H, MeO, 200° (EtOH); 2, H, H, Me, H, MeO, 216° (EtOH); 3, Me, H, H, H, MeO, 218° (CH₂Cl₂); (1) bis(acid maleate) m. 155° (iso-PrOH), (2) bis(acid maleate) m. 155°  The following II were also prepd.:  n, R, R¹, R², m.p.; 1, Me, A(R = R¹ = X = Y = H,Z =Cl), A(R = R¹ = X = Z = H,Y = Cl), 208-10° (HCONMe₂); 1, Me, A(R = R¹ = X = Y= H, Z = Cl), A(R = R¹ = X = Y = H,Z = MeO), 206-8° (HCONMe₂); 1, Me, A(R¹ = X = Y = H, R = 4-ClC₆H₄, Z = Cl), A(R = R¹ = X = Y = H,Z = Cl, 230-2° (HCONMe₂)  The following III were prepd.:  n, R, m, R¹, R², m.p.; 3, Me, 1, H, A(R = R¹ = X = Y = H, Z= Cl), 190-1° and 213-15°; 2, H, 2, H, A(R = X = Y = H, R¹ = Me, Z =Cl), 198° (PrOH); 3, Me, 2, H, A(R = R¹ = X = Y = H,Z = Cl), 160-2°; 1, Me, 1, H, A(R = R¹ = X = Y = H,Z = Cl), 178°; 1, Me, 1, Me, A(R¹ = X = Z = H,R = Me, Y =AcNH), 330° (decompn.) (EtOH); 2, H, 2, H, A(R¹ = X = Y = H,R = 4-ClC₆H₄,Z = Cl), 320-1° (HCONMe₂); 2, H, 2, H, A(R = Y = Z = H, R¹ = Me, X = Cl) 96° (iso-PrOH); 1, Me, 1, Me, A(R = R¹ = X = Z = H, Y = Cl), 220° and 246-8°; 1, Me, 1, Me, A(R¹ = X = Z = H, R = Me, Y = NH₂), 305° (EtOH-H₂O); 1, Me, 1, Me, A(R¹ = X = Z = H, R = Me, Y = MeO, 244° (EtOH)  Also prepd. were (m.p. given): 1,4-bis[2-(7-chloro-4-quinolylamino)propyl]hexahydro-1,4-diazepine, 169°; 1-[5-(7-chloro-4-quinolylamino)-2-pentyl]-4-[2-(7-chloro-4-quinolylamino)propyl] piperazine, 210-12°(HCONMe₂); 1,4-bis[3-(7-chloro- 4-quinolylamino)propyl] hexahydro-1,4-diazepine, 186° (HCONMe₂).  The following were prepd. (m.p. and optical rotation given):L(+)-1,4-bis[2-(7-chloro-4-quinolylamino)propyl]piperazine, 250-1°, [α]^23.5_D 382° ± 1° (c 4, 50:50 MeOH-H₂O); D(-)-1,4- bis[2-(7-chloro-4-quinolylamino)propyl] piperazine, 250-1°, [α]²⁵_D -382.5° ± 1° (c 4, 50:50 MeOH-H₂O); DL-1,4-bis[2-(7-chloro-4-quinolylamino)propyl]piperazine (IV), 266-8°, -; meso-1,4-bis [2-(7-chloro-4-quinolylamino)propyl] piperazine (V), 270-1° (HCONMe₂), -; equimol. mixt. of IV and V, 250-2°, -; 1,4-bis[2-(6-chloro-4-quinolylamino)propyl]piperazine-form A (VI-form A), 227° -; VI-form B, 110° and 245°, -.  Also prepd. are the following intermediates of the general formula VII (R = H) (X, Y, Z, and m.p. given): OH, H, SO₂NMe₂, ∼288°; Cl, H,SO₂NMe₂, 170°; HO(CH₂)₃CHMeNH, H, H, 158° (EtOH); AcO(CH₂)₃CHMeNAc, H, H, -; HO(CH₂)₃CHMeNAc, H, H, -; MeSO₃(CH₂)₃CHMeNAc, H, H, -; N-(5-piperazino-2-pentyl)acetamido, H, H, -; HO(CH₂)₃CHMeNH, MeO, H, -; AcO(CH₂)₃CHMeNAc, MeO, H, -; HO(CH₂)₃CHMeNAc, MeO, H, -; MeSO₃(CH₂)₃CHMeNAc, MeO, H, -; N-(5-piperazino-2-pentyl)acetamido, MeO, H, -; Me(HOCH₂)CH, H, Cl, 210°; Me(ClCH₂)CH, H, Cl, 148-50°; Me(HOCH₂)CH, Cl, H, 192°; Me(ClCH₂)CH, Cl, H, 142°; Me(HOCH₂)CH, H, MeO, 170°; Me(ClCH₂)CH, H, MeO, 160°.  Also prepd. were (m.p. given): VII (R = CO₂Et, X = OH, Y = H, Z = SO₂NMe₂), ∼335°; VII (R = CO₂H, X = OH, Y = H, Z = SO₂HMe₂), 310° (decompn.); 1,4-bis(2-oxopropyl)hexahydro-1,4-diazepine, -; 1,4-bis(2-oximinopropyl)hexahydro-1,4-diazepine, 180-1°; 1,4-bis(2-aminopropyl)hexahydro-1,4-diazepine, -; 1,4-bis(2-cyanoethyl)-hexahydro-1,4-diazepine, -.  The following were prepd. (m.p. and optical rotation given): L(+)-4-(3-hydroxy-2-propylamino)-7-chloroquinoline, 223-4°, [α]²⁴_D 28.5° ± 2° (c 1, EtOH); L(+)-4-(3-chloro-2-propylamino)-7-chloroquinoline, 146-7°, [α]²⁴_D 103 ± 1° (c 2, EtOH); L(+)-4-(3-piperazino-2-propylamino)-7-chloroquinoline, 128-30°, [α]²³_D 139 ± 1° (c 2, EtOH); D(-)-4-(3-hydroxy-2-propylamino)-7-chloroquinoline, 223-4°, [α]²⁵_D – 31 ± 2° (c 1, EtOH); D(-)-4-(3-chloro-2-propylamino)-7-chloroquinoline, 147-8°, [α]²⁴_D -101 ± 1° (c 2, EtOH); D(-)-4-(3-piperazino-2-propylamino)-7-chloroquinoline, 131-2°, [α]²³_D -137 ± 1° (c 2, EtOH)

PATENT

FR CAM42 19631007.

Patent Information

BE 612207

////////////////Dichlorquinazine, BRN 0867697, Dichlorquinazine, EINECS 234-130-6, NSC 129790, RP 12278, UNII-HT3GAD2SCM, WR 3863

CC(C)(NC1=C2C=CC(=CC2=NC=C1)Cl)N3CCN(CC3)C(C)(C)NC4=C5C=CC(=CC5=NC=C4)Cl

WRONG

CC(CN1CCN(CC(C)Nc2ccnc3cc(Cl)ccc23)CC1)Nc4ccnc5cc(Cl)ccc45.CS(=O)(=O)O

AND

Clc1ccc2c(c1)nccc2NC(C)CN1CCN(CC(C)Nc2ccnc3cc(Cl)ccc32)CC1

CORRECT