Sodium borohydride → 4-Hydroxyl-[5-({[5-methyl-1-(4-methylphenyl)-1H-pyrazol-4-yl]carbonyl}amino)pyridin-2-yl]cyclohexanecarboxylic acid ethyl ester

HRID 1748637Notes

Reaction equation

HRID 1748637 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6]([C:8]1([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[CH:25]=[N:26][N:27]([C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)[C:28]=3[CH3:29])=[O:23])=[CH:17][N:16]=2)[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])[CH3:4]>CO.C(Cl)(Cl)Cl>[CH2:3]([O:5][C:6]([C:8]1([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[CH:25]=[N:26][N:27]([C:30]4[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=4)[C:28]=3[CH3:29])=[O:23])=[CH:17][N:16]=2)[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])[CH3:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 866925731-[5-({[5-methyl 1-(4-methylphenyl)-1H-pyrazol-4-yl]carbonyl}amino)pyridin-2-yl]-4-oxocyclohexanecarboxylic acid ethyl ester

Product 1

HCID 866925744-Hydroxyl-[5-({[5-methyl-1-(4-methylphenyl)-1H-pyrazol-4-yl]carbonyl}amino)pyridin-2-yl]cyclohexanecarboxylic acid ethyl esterYield 70.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

Sodium borohydride (131 mg) was added at −78° C. to a solution of 1-[5({[5-methyl-1-(4-methylphenyl)-1H-pyrazol-4-yl]carbonyl}amino)pyridin-2-yl]-4-oxocyclohexanecarboxylic acid ethyl ester (400 mg) in methanol (6.0 ml) and chloroform (3.0 ml) and stirred at the same temperature for four hours. After the reaction, a saturated aqueous solution of ammonium chloride, the solvent was evaporated and extracted with chloroform three times. The organic solution was dried over anhydrous magnesium sulfate and concentrated. The resulting residue was recrystallized (n-hexane/ethanol) to give the titled compound (284 mg) as a white solid. MS (ESI) m/z: 463 (M+H)+.

Workup

  1. customAfter the reaction
  2. customa saturated aqueous solution of ammonium chloride, the solvent was evaporated
  3. extractionextracted with chloroform three times
  4. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was recrystallized (n-hexane/ethanol)

Sources & evidence

ORD record
ord-bdd71081afd947e587d5fdc2ab2d4026
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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