Potassium Carbonate → 2-(1-(2-(2,4-Difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-indazol-5-ylamino)-N-(2,6-dimethylphenyl)acetamide

HRID 1159003Notes

Reaction equation

HRID 1159003 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[F:27])([OH:19])[CH2:13][N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)[N:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][C:36]([NH:38][C:39]1[C:44]([CH3:45])=[CH:43][CH:42]=[CH:41][C:40]=1[CH3:46])=[O:37]>>[F:27][C:21]1[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:20]=1[C:12]([OH:19])([CH2:13][N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)[CH2:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([NH:1][CH2:35][C:36]([NH:38][C:39]3[C:44]([CH3:45])=[CH:43][CH:42]=[CH:41][C:40]=3[CH3:46])=[O:37])=[CH:10][CH:9]=2)[CH:5]=[N:6]1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27634872-bromo-N-(2,6-dimethylphenyl)acetamideHCID 68644438(5-Amino-1H-indazol-1-yl)-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol

Product 1

HCID 686449082-(1-(2-(2,4-Difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-1H-indazol-5-ylamino)-N-(2,6-dimethylphenyl)acetamideYield 50%

Procedure

To a solution of (5-amino-1H-indazol-1-yl)-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol (0.1 g, 0.27 mmol) in N,N-dimethylformaide (1 ml) was slowly added potassium carbonate (0.037 g, 0.27 mmol) at 0° C. and followed by stirring for 30 min. The addition of 2-bromo-N-(2,6-dimethylphenyl)acetamide (0.065 g, 0.27 mmol) to the solution was followed by stirring at room temperature for hours and concentrated by evaporation in a vacuum condition. The crude product was purified by chromatography on silica gel to give the title compound (Yield 50%).

Workup

  1. customat 0° C.
  2. stirringby stirring at room temperature for hours
  3. concentrationconcentrated by evaporation in a vacuum condition
  4. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a8fe5043ed7d4eada16deb0575e1cc31
Source dataset
uspto-grants-2010_10
Patent number
US07812045B2

Reaction notes

Loading…