2-Bromoethanol → HCID 71599857, compound

HRID 2167781Notes

Reaction equation

HRID 2167781 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-819691958f11492a870186ab3dc951d2
Source dataset
uspto-grants-2015_06
Patent number
US09045479B2

Reaction notes

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