2-(Cbz-Amino)-5-methylpyrazine

Benzyl (5-methylpyrazin-2-yl)carbamate

CAS 1033418-57-3

Mp 191.4 °C.

IR 1719, 1567, 1353, 1226, 1054, 759, 744, 706 cm^–1.

¹H NMR (DMSO-d₆, 500 MHz) 10.45 (br, 1H), 8.93 (s, 1H), 8.20 (s, 1H), 7.42–7.32 (m, 5H), 5.18 (s, 2H), 2.41 (s, 3H).

¹³C NMR (DMSO-d₆, 125.7 MHz) 153.6, 147.7, 146.7, 141.7, 136.5, 134.3, 128.7 (2C), 128.4, 128.2 (2C), 66.5, 20.4.

HRMS elemental calculated for C₁₃H₁₄N₃O₂ (MH⁺): 244.1086; found: 244.1080.

NMR PREDICT

1H NMR

13 C NMR PREDICT

Use of a Curtius Rearrangement as Part of the Multikilogram Manufacture of a Pyrazine Building Block

Alan Steven^*†  and Phillip Hopes^‡

^† Pharmaceutical Technology & Development, AstraZeneca, Charter Way, Macclesfield, SK10 2NA, United Kingdom

^‡ Cyton Biosciences Ltd., 68 Macrae Road, Bristol, BS20 0DD, United Kingdom

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/acs.oprd.7b00340

*E-mail: Alan.Steven@astrazeneca.com.

http://pubs.acs.org/doi/10.1021/acs.oprd.7b00340

A modular flow reactor for performing Curtius rearrangements as a continuous flow process

Marcus Baumann,^a  Ian R. Baxendale,^a  Steven V. Ley,*^a  Nikzad Nikbin,^a  Christopher D. Smith^a  and Jason P. Tierney^b 

*Corresponding authors

^aInnovative Technology Centre, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK
E-mail: svl1000@cam.ac.uk
Fax: +44 1223 336442
Tel: +44 1223 336398

^bNeurology Lead Discovery Chemistry, Neurology CEDD, GlaxoSmithKline R and D, New Frontiers Science Park (North), Third Avenue, Harlow, UK

Abstract

The use of a mesofluidic flow reactor is described for performing Curtius rearrangement reactions of carboxylic acids in the presence of diphenylphosphoryl azide and trapping of the intermediate isocyanates with various nucleophiles.

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O=C(OCc1ccccc1)Nc2cnc(C)cn2