2-Bromoethanol → HCID 71599857, compound

HRID 926718Notes

Reaction equation

HRID 926718 reaction equation
Br[CH2:2][CH2:3][OH:4].[F:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[C@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]1[CH:23]=[CH:22][N:21]2[N:24]=[CH:25][C:26]([C:27]([NH:29][CH:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)=[O:28])=[C:20]2[CH:19]=1>C(#N)C.CCOC(C)=O>[F:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[C@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]1[CH:23]=[CH:22][N:21]2[N:24]=[CH:25][C:26]([C:27]([NH:29][CH:30]3[CH2:35][CH2:34][N:33]([CH2:2][CH2:3][OH:4])[CH2:32][CH2:31]3)=[O:28])=[C:20]2[CH:19]=1

Participants

5

Reactant 2

HCID 108982-BromoethanolHCID 89618564HCID 89618564, compound

Product 1

HCID 71599857HCID 71599857, compoundYield 7.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromoethanol (18 mg, 0.14 mmol) was added to stirred solution of (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-N-(piperidin-4-yl)pyrazolo[1,5-a]pyridine-3-carboxamide (50 mg, 0.12 mmol) (Example-32) in acetonitrile (0.5 mL) and stirring was continued at 70° C. for 4 h. The reaction mixture was diluted with EtOAc, washed the organic layer with water and dried over anhydrous sodium sulphate, concentrated under reduced pressure to afford the crude product, which was purified by Preparative HPLC [Column: 21.2×150×5 um, waters×bridge C-18, Mobile phase-A: 0.1% TFA in water, B: ACN, Gradient (Time/% B): 0/20, 2/30, 1870 and Flow rate: 20 mL/min] to afford 4.1 mg of the title compound.

Workup

  1. washwashed the organic layer with water
  2. dry with materialdried over anhydrous sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude product, which
  5. customwas purified by Preparative HPLC [Column: 21.2×150×5 um, waters×bridge C-18, Mobile phase-A: 0.1% TFA in water, B: ACN, Gradient (Time/% B): 0/20, 2/30, 1870 and Flow rate: 20 mL/min]

Sources & evidence

ORD record
ord-b2471be18e6d4a13a204313930858cc0
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

Loading…