Dimethylformamide → (S)-N-(4-Chloro-3-(3-(4-chloro-5-(2-(methoxymethyl)pyrrolidin-1-yl)-2-nitrophenyl)thioureido)benzyl)-1-(trifluoromethyl)cyclopropanecarboxamide

HRID 1258751Notes

Reaction equation

HRID 1258751 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:5][NH:6][C:7]([C:9]1([C:12]([F:15])([F:14])[F:13])[CH2:11][CH2:10]1)=[O:8].[Cl:20][C:21]1[C:22]([N:33]2[CH2:37][CH2:36][CH2:35][C@H:34]2[CH2:38][O:39][CH3:40])=[CH:23][C:24]([N:30]=[C:31]=[S:32])=[C:25]([N+:27]([O-:29])=[O:28])[CH:26]=1.CN(C=O)C>[Cl-].[Na+].O>[Cl:19][C:18]1[CH:17]=[CH:16][C:4]([CH2:5][NH:6][C:7]([C:9]2([C:12]([F:13])([F:14])[F:15])[CH2:10][CH2:11]2)=[O:8])=[CH:3][C:2]=1[NH:1][C:31]([NH:30][C:24]1[CH:23]=[C:22]([N:33]2[CH2:37][CH2:36][CH2:35][C@H:34]2[CH2:38][O:39][CH3:40])[C:21]([Cl:20])=[CH:26][C:25]=1[N+:27]([O-:29])=[O:28])=[S:32]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 59529866N-(3-amino-4-chlorobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamideHCID 86674357(S)-5-chloro-2-isothiocyanato-4-(2-(methoxymethyl)pyrrolidin-1-yl)-nitrobenzene

Product 1

HCID 86674356(S)-N-(4-Chloro-3-(3-(4-chloro-5-(2-(methoxymethyl)pyrrolidin-1-yl)-2-nitrophenyl)thioureido)benzyl)-1-(trifluoromethyl)cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of N-(3-amino-4-chlorobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamide (150 mg; 0.51 mmol), (S)-5-chloro-2-isothiocyanato-4-(2-(methoxymethyl)pyrrolidin-1-yl)-nitrobenzene (169 mg; 0.51 mmol) and DMF (3 mL) was stirred at rt overnight. The mixture was poured into brine and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was washed with Et2O to give the sub-title compound.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washThe residue was washed with Et2O

Sources & evidence

ORD record
ord-4d0a0d7153f04893827f65fa5ae39a26
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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