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

HRID 539075노트

반응식

HRID 539075 반응식
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

참가 물질

8

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-40f0b8cbd2cd468ba7220508d989dc70
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865726B2

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