Stannous Chloride → N-(3-amino-4-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)phenyl)-4-chlorobenzamide

HRID 1529488

Reaction equation

HRID 1529488 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:19]([CH3:20])[N:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)=[C:11]([N+:25]([O-])=O)[CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[Sn](Cl)Cl>CO>[NH2:25][C:11]1[CH:10]=[C:9]([NH:8][C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:29][CH:28]=2)[CH:14]=[CH:13][C:12]=1[C:15]1[N:19]([CH3:20])[N:18]=[C:17]([C:21]([F:24])([F:22])[F:23])[CH:16]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 674670954-chloro-N-(4-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-3-nitrophenyl)benzamide

Product 1

HCID 67464229N-(3-amino-4-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)phenyl)-4-chlorobenzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 16 (42 mg, 0.1 mmol) was dissolved in 10 ml MeOH. Tin(II)chloride dehydrate (223 mg, 1 mmol) was added and the reaction mixture was stirred at r.t. for overnight. The reaction mixture was evaporated to dryness. The solid residue was dissolved in 6 N NaOH and extracted with DCM. The org. phase was washed with brine. After concentrated to dryness, the solid residue was dissolved in DMF and purified on prep HPLC to give compound 17.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionThe solid residue was dissolved in 6 N NaOH
  3. extractionextracted with DCM
  4. washphase was washed with brine
  5. concentrationAfter concentrated to dryness
  6. dissolutionthe solid residue was dissolved in DMF
  7. custompurified on prep HPLC

Sources & evidence

ORD record
ord-f7e25a5fe4e647148fcd7e68fe4c4410
Source dataset
uspto-grants-2015_07
Patent number
US09090612B2

Linked notes

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