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

HRID 1748637노트

반응식

HRID 1748637 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6212Chloroform용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-bdd71081afd947e587d5fdc2ab2d4026
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150555B2

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