Triethylamine → (S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide

HRID 539075ノート

反応式

HRID 539075 の反応式
C(N=C=NCCCN(C)C)C.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C@H:19]2[CH2:23][O:22][C:21](=[O:24])[N:20]2[C:25]2[CH:30]=[CH:29][N:28]3[N:31]=[CH:32][C:33]([C:34]4[CH:42]=[CH:41][C:37]([C:38]([OH:40])=O)=[CH:36][CH:35]=4)=[C:27]3[N:26]=2)=[CH:15][CH:14]=1.OC1C2N=[N:50][NH:49]C=2C=CC=1.O.NN.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C@H:19]2[CH2:23][O:22][C:21](=[O:24])[N:20]2[C:25]2[CH:30]=[CH:29][N:28]3[N:31]=[CH:32][C:33]([C:34]4[CH:42]=[CH:41][C:37]([C:38]([NH:49][NH2:50])=[O:40])=[CH:36][CH:35]=4)=[C:27]3[N:26]=2)=[CH:15][CH:14]=1

参加物

8

反応物 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 24654Hydrazine hydrate (1:1)HCID 67034785(S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoic acidHCID 178418300HCID 178418300、化合物

生成物 1

HCID 67035490(S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide収率 79%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (0.1031 g, 0.5378 mmol) was added to a mixture of (S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoic acid (0.075 g, 0.1793 mmol) and hydroxybenzotriazole (0.073 g, 0.5378 mmol) in DMF (0.6 mL) at ambient temperature. After stirring for 10 minutes, hydrazine monohydrate (0.02609 mL, 0.5378 mmol), followed by triethylamine (0.07496 mL, 0.5378 mmol) were added. The mixture was stirred at ambient temperature for 4 hours, diluted with EtOAc, washed with aqueous saturated NH4Cl, brine, dried (phase separator silicone treated filter paper), concentrated and purified on silica gel (2-8% MeOH in DCM) to provide (S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide (0.061 g, 79% yield) as a clear oil.

後処理

  1. additionwere added
  2. stirringThe mixture was stirred at ambient temperature for 4 hours
  3. washwashed with aqueous saturated NH4Cl, brine
  4. customdried
  5. addition(phase separator silicone treated filter paper)
  6. concentrationconcentrated
  7. custompurified on silica gel (2-8% MeOH in DCM)

出典と根拠

ORDレコード
ord-40f0b8cbd2cd468ba7220508d989dc70
出典データセット
uspto-grants-2014_10
特許番号
US08865726B2

反応ノート

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