Ammonium Chloride → (S)-N-(3-(3-(2-Amino-4-chloro-5-(2-(methoxymethyl)pyrrolidin-1-yl)phenyl)thioureido)-4-chlorobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamide

HRID 1258752Notes

Reaction equation

HRID 1258752 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[NH:19][C:20]([NH:22][C:23]1[CH:28]=[C:27]([N:29]2[CH2:33][CH2:32][CH2:31][C@H:30]2[CH2:34][O:35][CH3:36])[C:26]([Cl:37])=[CH:25][C:24]=1[N+:38]([O-])=O)=[S:21].[NH4+].[Cl-]>[Fe].CCO>[NH2:38][C:24]1[CH:25]=[C:26]([Cl:37])[C:27]([N:29]2[CH2:33][CH2:32][CH2:31][C@H:30]2[CH2:34][O:35][CH3:36])=[CH:28][C:23]=1[NH:22][C:20](=[S:21])[NH:19][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:2]=1[Cl:1])[CH2:6][NH:7][C:8]([C:10]1([C:13]([F:16])([F:15])[F:14])[CH2:11][CH2:12]1)=[O:9]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 86674356(S)-N-(4-Chloro-3-(3-(4-chloro-5-(2-(methoxymethyl)pyrrolidin-1-yl)-2-nitrophenyl)thioureido)benzyl)-1-(trifluoromethyl)cyclopropanecarboxamide

Product 1

HCID 86674358(S)-N-(3-(3-(2-Amino-4-chloro-5-(2-(methoxymethyl)pyrrolidin-1-yl)phenyl)thioureido)-4-chlorobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (S)—N-(4-chloro-3-(3-(4-chloro-5-(2-(methoxymethyl)pyrrolidin-1-yl)-2-nitrophenyl)thioureido)benzyl)-1-(trifluoromethyl)cyclopropanecarboxamide (145 mg; 0.23 mmol), Fe (65 mg; 1.2 mmol), saturated aqueous NH4Cl-solution (3 mL) and EtOH (3 mL) was stirred at 90° C. for 2 h. The mixture was basicified to pH-9-10 and filtered through celite. The celite pad was washed with EtOH and EtOAc. The mixture was concentrated and the residue was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was washed with Et2O to give the sub-title compound.

Workup

  1. filtrationfiltered through celite
  2. washThe celite pad was washed with EtOH and EtOAc
  3. concentrationThe mixture was concentrated
  4. extractionthe residue was extracted with EtOAc
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washThe residue was washed with Et2O

Sources & evidence

ORD record
ord-319a60ff269c4968a7a269ed776812f6
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

Loading…