Reaction #73635

ord-21b509c3d6944a42a73670d742415383

Reaction equation

COc1ccc(C(=O)Cl)cc1
4-methoxybenzoyl chloride
Cc1nc(N)sc1C(=O)NCc1ccccc1
2-amino-4-methylthiazole-5-carboxylic acid benzylamide
COc1ccc(C(=O)Nc2nc(C)c(C(=O)NCc3ccccc3)s2)cc1
title compound
Yield 10.0%
COc1ccc(C(=O)Nc2nc(C)c(C(=O)NCc3ccccc3)s2)cc1
2-(4-Methoxybenzoylamino)-4-methylthiazole-5-carboxylic Acid Benzylamide
Yield 10.0%

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Following the procedure as described in Example 2, making variations only as required to use 4-methoxybenzoyl chloride in place of benzoyl chloride to react with 2-amino-4-methylthiazole-5-carboxylic acid benzylamide, the title compound was obtained as a white solid in 10% yield; m.p. 203-204° C.; 1H NMR (CDCl3, 300 MHz) δ 7.86 (d, J=8.8 Hz, 2H), 7.35-7.30 (m, 5H), 6.96 (d, J=8.8 Hz, 2H), 5.97 (t, J=5.6 Hz, 1H), 4.58 (d, J=5.6 Hz, 2H), 3.86 (s, 3H), 2.49 (s, 3H); MS (ES+) m/z 382.1 (M+1).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08541457B2uspto-grants-2013_09