Reaction #1904067

ord-78457ded9542445e88a562c530f2a867

Reaction equation

CC1OCC(=O)Nc2ccc(-c3cccn3C(=O)OC(C)(C)C)cc21
tert-butyl-2-(5-methyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-1H-pyrrole-1-carboxylate
O=C=NS(=O)(=O)Cl
chlorosulfonyl isocyanate
CC1OCC(=O)Nc2ccc(-c3ccc(C#N)n3C(=O)OC(C)(C)C)cc21
tert-Butyl-2-cyano-5-(5-methyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-1H-pyrrole-1-carboxylate

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

tert-Butyl-2-cyano-5-(5-methyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-1H-pyrrole-1-carboxylate was prepared from tert-butyl-2-(5-methyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-1H-pyrrole-1-carboxylate and chlorosulfonyl isocyanate according to the cyanation procedure described in example 1. 1H-NMR (DMSO-d6) δ 10.30 (s, 1H), 7.37-7.25 (m, 3H), 7.16 (d, J=8.26 Hz, 1H), 6.46 (d, J=3.77 Hz, 1H), 4.81 (q, J=6.14 Hz, 1H), 4.47 (d, J=16.42 Hz, 1H), 4.36 (d, J=16.44 Hz, 1H), 1.51 (d, J=6.48 Hz, 3H), 1.37 (s, 9H); MS (ES) m/z 366 ([M−H]−, 100%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07598237B2uspto-grants-2009_10