Methanol → HCID 86729423, compound

HRID 521246Notes

Reaction equation

HRID 521246 reaction equation
[C:1]([CH2:3][C:4]1([N:11]2[CH:15]=[C:14]([C:16]([NH2:18])=[O:17])[C:13]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[N:12]2)[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1)#[N:2].CO.[BH4-].[Na+]>C1COCC1.CCOC(C)=O.O>[C:1]([CH2:3][C:4]1([N:11]2[CH:15]=[C:14]([C:16]([NH2:18])=[O:17])[C:13]([NH:19][C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)=[N:12]2)[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1)#[N:2]

Participants

7

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86729422HCID 86729422, compound

Product 1

HCID 86729423HCID 86729423, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-[1-(cyanomethyl)-4-oxocyclohexyl]-3-[(4-fluorophenyl)amino]-1H-pyrazole-4-carboxamide (90 mg, 0.25 mmol) in a mixture of THF (1.9 mL)/MeOH (0.6 mL) at 0° C. was added NaBH4 (10 mg, 0.25 mmol), and the mixture was stirred at 0° C. for 10 minutes, then warmed to ambient temperature and stirred for another 10 minutes. The mixture was diluted with EtOAc and H2O. The organic layer was separated, washed with saturated aqueous NH4Cl, brine, dried over anhydrous MgSO4, and concentrated in vacuo. The crude residue containing a mixture of the two diasteromeric alcohols was used for next step without purification. LRMS (ESI) calc'd for C18H20FN5O2 [M+H]+: 358. Found: 358.

Workup

  1. temperaturewarmed to ambient temperature
  2. stirringstirred for another 10 minutes
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous NH4Cl, brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo
  7. additionThe crude residue containing
  8. additiona mixture of the two diasteromeric alcohols
  9. customwas used for next step without purification

Sources & evidence

ORD record
ord-0da46bd88b06488f95c3fec9249ee5cf
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

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