Sodium borohydride → HCID 136928068, compound

HRID 64298Notes

Reaction equation

HRID 64298 reaction equation
[C:1]([C:3]1[C:4]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:23][CH:22]=2)=[N:5][N:6]2[C:11]([CH2:12][N:13](C)[C:14](=O)C(F)(F)F)=[CH:10][CH:9]=[N:8][C:7]=12)#[N:2].[BH4-].[Na+]>CCO>[CH3:14][NH:13][CH2:12][CH:11]1[N:6]2[N:5]=[C:4]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:23][CH:22]=3)[C:3]([C:1]#[N:2])=[C:7]2[NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 117668117HCID 117668117, compound

Product 1

HCID 136928068HCID 136928068, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-((3-cyano-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl)methyl)-2,2,2-trifluoro-N-methylacetamide (40 mg, 0.089 mmol) in 15 mL of EtOH was added NaBH4 (50 mg). After stirring at rt for 30 mins, the mixture was concentrated. The residue was partitioned between 20 mL of water and 20 mL of EA. The EA layer was concentrated and purified by Pre-TLC (DCM/MeOH=5/1) to give a white solid (20 mg, 63%). MS (ESI) m/e [M+1]+ 359.9.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was partitioned between 20 mL of water and 20 mL of EA
  3. concentrationThe EA layer was concentrated
  4. custompurified by Pre-TLC (DCM/MeOH=5/1)

Sources & evidence

ORD record
ord-82797490dc134460ac954fcf2e4947d9
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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