Diisopropylcarbodiimide → HCID 46908542, compound

HRID 1410242Notes

Reaction equation

HRID 1410242 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[CH:24]=[C:25]([CH:36]=[CH:37][C:38]=1[NH:39][CH2:40][CH2:41][N:42]([CH3:44])[CH3:43])[C:26]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][CH:30]=1)=[O:27].CC(C)N=C=NC(C)C>CN(C=O)C>[Br:35][C:32]1[CH:33]=[CH:34][C:29]([NH:28][C:26]([C:25]2[CH:36]=[CH:37][C:38]3[N:39]([CH2:40][CH2:41][N:42]([CH3:44])[CH3:43])[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:22][C:23]=3[CH:24]=2)=[O:27])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 59529864HCID 59529864, compoundHCID 86646336N-(4-Chloro-3-isothiocyanatobenzyl)-1-(trifluoromethyl)cyclopropane carboxamide

Product 1

HCID 46908542HCID 46908542, 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 ((222 mg; 0.66 mmol) see Example 59, step (c)), 3-amino-N-(4-bromophenyl)-4-(2-(dimethylamino)ethylamino)benzamide (250 mg; 0.66 mmol), DIC (83 mg; 0.66 mmol) and DMF (4 mL). Yield: 151 mg (34%). 400 MHz 1H-NMR (DMSO-d6, ppm) 10.37 (1H, s) 10.22 (1H, s) 8.39 (1H, t, J=5.8 Hz) 8.10 (1H, d, J=1.8 Hz) 8.06 (1H, d, J=1.6 Hz) 7.82-7.71 (3H, m) 7.53-7.46 (3H, m) 7.40 (1H, d, J=8.2 Hz) 6.86 (1H, dd, J=8.2, 1.8 Hz) 4.32-4.21 (4H, m) 2.74-2.68 (2H, m) 2.29 (6H, s) 1.37-1.32 (2H, m) 1.23-1.19 (2H, m).

Sources & evidence

ORD record
ord-af95dcb9b03e4399b9d50e9e750e13d2
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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