Diisopropylcarbodiimide → HCID 178486904, compound

HRID 1410238Notes

Reaction equation

HRID 1410238 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]([C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[N:19]=[C:20]=S.[NH2:22][C:23]1[C:38]([NH2:39])=[CH:37][C:26]([C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([Br:36])=[CH:32][CH:31]=2)=[O:28])=[C:25]([O:40][CH3:41])[CH:24]=1.CC(C)N=C=NC(C)C>CN(C=O)C>[Br:36][C:33]1[CH:32]=[CH:31][C:30]([NH:29][C:27]([C:26]2[C:25]([O:40][CH3:41])=[CH:24][C:23]3[NH:22][C:20]([NH:19][C:3]4[CH:4]=[C:5]([CH2:6][NH:7][C:8]([C:10]5([C:13]([F:16])([F:15])[F:14])[CH2:12][CH2:11]5)=[O:9])[CH:17]=[CH:18][C:2]=4[Cl:1])=[N:39][C:38]=3[CH:37]=2)=[O:28])=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 595298704,5-diamino-N-(4-bromophenyl)-2-methoxybenzamideHCID 86646336N-(4-Chloro-3-isothiocyanatobenzyl)-1-(trifluoromethyl)cyclopropane carboxamide

Product 1

HCID 178486904HCID 178486904, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared in accordance with the procedure in Example 72, step (a) using N-(4-chloro-3-isothiocyanatobenzyl)-1-(trifluoromethyl)cyclopropane carboxamide ((200 mg; 0.60 mmol) see Example 59, step (c)), 4,5-diamino-N-(4-bromophenyl)-2-methoxybenzamide (202 mg; 0.60 mmol), DIC (76 mg; 0.60 mmol) and DMF (4 mL). Yield: 63 mg (16%). 400 MHz 1H-NMR (DMSO-d6, ppm) 11.12 (0.36H, s, minor tautomer) 11.00 (0.57H, s, major tautomer) 10.22-10.14 (1H, m) 8.94 (0.57H, s, major tautomer) 8.76 (0.36H, s, minor tautomer) 8.61-8.52 (1H, m) 8.48-8.41 (1H, m) 7.86-7.69 (3H, m) 7.53-7.45 (2H, m) 7.42-7.35 (1H, m) 7.21 (0.38H, s, minor tautomer) 7.10 (0.59H, s, major tautomer) 6.87-6.79 (1H, m) 4.29 (2H, d, J=5.8 Hz) 3.93 (3H, s) 1.49-1.39 (2H, m) 1.28-1.23 (2H, m). MS m/z: 636, 638, 640 [M+H]+.

Sources & evidence

ORD record
ord-832cfd6086fe495d94b955f35c20473f
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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