Water → (R)-N-(1-(5-bromo-2-(methylsulfonyl)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)-2-(3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamide

HRID 2170324Notes

Reaction equation

HRID 2170324 reaction equation
[Br:1][C:2]1[C:3]([C@H:10]([NH:20][C:21](=[O:36])[CH2:22][N:23]2[C:31]3[CH2:30][CH2:29][CH2:28][CH2:27][C:26]=3[C:25]([C:32]([F:35])([F:34])[F:33])=[N:24]2)[CH2:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=2)=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:42].[OH2:48]>ClCCl>[Br:1][C:2]1[C:3]([C@H:10]([NH:20][C:21](=[O:36])[CH2:22][N:23]2[C:31]3[CH2:30][CH2:29][CH2:28][CH2:27][C:26]=3[C:25]([C:32]([F:35])([F:34])[F:33])=[N:24]2)[CH2:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=2)=[N:4][C:5]([S:8]([CH3:9])(=[O:42])=[O:48])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 90281265(R)-N-(1-(5-bromo-2-(methylthio)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)-2-(3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamide

Product 1

HCID 90281548(R)-N-(1-(5-bromo-2-(methylsulfonyl)pyrimidin-4-yl)-2-(3,5-difluorophenyl)ethyl)-2-(3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 11G (198 mg, 0.33 mmol) was charged in dichloromethane (2 ml) at 0° C. mCPBA (meta-chloroperoxybenzoic acid) (185 mg, 0.8 mmol, content 77 percent; 2.5 eq.) was added a little at a time. The mixture was slowly warmed to room temperature and stirred for 4 h and then water was added. The reaction mixture was partitioned between dichloromethane and saturated NaHCO3 aqueous solution. The organic layer was separated and concentrated to afford the title product. MS (m/z) 622.98 [M+H]+.

Workup

  1. additionwas added a little at a time
  2. customThe reaction mixture was partitioned between dichloromethane and saturated NaHCO3 aqueous solution
  3. customThe organic layer was separated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-92707762d5c94c30928ae5d783a2fe7a
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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