Acetic Acid → tert-Butyl {2-[(4-{1-[(1,5-dimethyl-1H-pyrazol-4-yl)methyl]piperidin-4-yl}benzoyl)amino]phenyl}carbamate

HRID 222410노트

반응식

HRID 222410 반응식
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([CH:8]=O)[CH:4]=[N:3]1.[NH:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:38]=[CH:37][C:19]([C:20]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:21])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([CH2:8][N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:38]=[CH:37][C:19]([C:20]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:21])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH:4]=[N:3]1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5796431,5-dimethyl-1H-pyrazole-4-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59830875Tert-butyl 2-[(4-piperidin-4-ylbenzoyl)amino]phenylcarbamate

생성물 1

HCID 59830880tert-Butyl {2-[(4-{1-[(1,5-dimethyl-1H-pyrazol-4-yl)methyl]piperidin-4-yl}benzoyl)amino]phenyl}carbamate수율 84%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1,5-Dimethyl-1H-pyrazole-4-carbaldehyde (114 mg, 0.92 mmol) was added to a solution of tert-butyl 2-[(4-piperidin-4-ylbenzoyl)amino]phenylcarbamate (289 mg, 0.73 mmol) in dichloromethane (6 ml) followed by acetic acid (50 μl, 0.87 mmol). The reaction mixture was allowed to stir under nitrogen for 2.5 hours. Sodium triacetoxyborohydride (233 mg, 1.10 mmol) was added and the reaction mixture allowed to stir, at ambient temperature, for 18 hours (overnight). Saturated aqueous sodium bicarbonate solution (10 ml) was then added to the reaction and allowed to stir for 15 minutes. The organic phase was separated and the aqueous phase re-extracted with dichloromethane (10 ml). The combined organics were washed with water, dried over magnesium sulphate and evaporated to dryness to afford the product as a colourless gum (308 mg, 84%), which was used without further purification; Mass Spectrum: M+H+504.

후처리

  1. stirringto stir, at ambient temperature, for 18 hours (overnight)
  2. stirringto stir for 15 minutes
  3. customThe organic phase was separated
  4. extractionthe aqueous phase re-extracted with dichloromethane (10 ml)
  5. washThe combined organics were washed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated to dryness

출처 및 근거

ORD 기록
ord-cdca534bab4c44b887943abca852c687
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207202B2

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