Sodium borohydride → HCID 73292408, compound

HRID 1398032Notes

Reaction equation

HRID 1398032 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=2)=[CH:12][C:11]([CH:23]2[CH2:28][C:27]([CH3:30])([CH3:29])[O:26][C:25]([CH3:32])([CH3:31])[CH2:24]2)=[N:10]1.[BH4-].[Na+]>C(O)C.CC#N.C(O)(C(F)(F)F)=O.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]([OH:22])[CH3:21])=[CH:16][CH:15]=2)=[CH:12][C:11]([CH:23]2[CH2:28][C:27]([CH3:30])([CH3:29])[O:26][C:25]([CH3:31])([CH3:32])[CH2:24]2)=[N:10]1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 73293256HCID 73293256, compound

Product 1

HCID 73292408HCID 73292408, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6342AcetonitrileSolventHCID 22392675Trifluoroacetic acid waterSolvent

Procedure

To a solution of 1-{4-[1-(2-methoxyphenyl)-3-(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-yl]-phenyl}-ethanone (Example 12) (20 mg, 0.05 mmol) in 1 mL of ethanol was added sodium borohydride (1.8 mg, 0.05 mmol) and the mixture stirred for 1 hr at RT. The solution was diluted with 5 mL of 50% CH3CN in 0.1% TFA/H2O and purified by RP-HPLC, eluting with a linear gradient of 50%-100% CH3CN in 0.1% TFA/H2O over 10 mins to give 20 mg (86%) of the title compound a white solid containing 0.5 eq of TFA.

Workup

  1. custompurified by RP-HPLC
  2. washeluting with a linear gradient of 50%-100% CH3CN in 0.1% TFA/H2O over 10 mins

Sources & evidence

ORD record
ord-a5124f3b6d564495bc7d3802dd30e69c
Source dataset
uspto-grants-2014_12
Patent number
US08901314B2

Reaction notes

Loading…