2-Fluoro-5-(trifluoromethyl)phenyl isocyanate → 3-{4-[({[2-Fluoro-5-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenyl}-5-({[(3-morpholin-4-ylpropyl)amino]carbonyl}amino)isothiazole-4-carboxamide

HRID 870995Notes

Reaction equation

HRID 870995 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([NH2:15])=[O:14])=[C:11]([NH:16][C:17]([NH:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[O:18])[S:10][N:9]=2)=[CH:4][CH:3]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][C:31]=1[N:40]=[C:41]=[O:42]>C(N(CC)C(C)C)(C)C>[F:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][C:31]=1[NH:40][C:41]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13]([NH2:15])=[O:14])=[C:11]([NH:16][C:17]([NH:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[O:18])[S:10][N:9]=2)=[CH:6][CH:7]=1)=[O:42]

Participants

4

Reactant 2

HCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 716213173-(4-Aminophenyl)-5-(3-(3-morpholinopropyl)ureido)isothiazole-4-carboxamide

Product 1

HCID 866892203-{4-[({[2-Fluoro-5-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenyl}-5-({[(3-morpholin-4-ylpropyl)amino]carbonyl}amino)isothiazole-4-carboxamideYield 62%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineCatalyst

Procedure

In a manner similar to that described for Example 3 (, 3-(4-aminophenyl)-5-(3-(3-morpholinopropyl)ureido)isothiazole-4-carboxamide (12 mg, 0.030 mmol), 3 drops N,N-diisopropylethylamine, and 2-fluoro-5-(trifluoromethyl)phenyl isocyanate (0.0087 mL, 0.060 mmol) was used to give the title compound as a white solid (11 mg, 62%).

Sources & evidence

ORD record
ord-78c8c7641b4143e69177360a9fb0c9d4
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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