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

HRID 1748637ノート

反応式

HRID 1748637 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6212Chloroform溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-bdd71081afd947e587d5fdc2ab2d4026
出典データセット
uspto-grants-2015_10
特許番号
US09150555B2

反応ノート

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