Acetic Acid → tert-Butyl (1S,2R)-2-(4-(1-ethyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate

HRID 516056노트

반응식

HRID 516056 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[CH:25]=[C:24]([C:26]#[N:27])[C:19]([C:20]([O:22]C)=O)=[C:18]([C:28]2[CH:29]=[N:30][N:31]([CH2:33][CH3:34])[CH:32]=2)[N:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(O)=O.C(=O)([O-])[O-].[K+].[K+]>CO.[Pd].C(Cl)Cl>[CH2:33]([N:31]1[CH:32]=[C:28]([C:18]2[C:19]3[C:20](=[O:22])[NH:27][CH2:26][C:24]=3[CH:25]=[C:16]([NH:15][C@@H:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C@@H:9]3[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[N:17]=2)[CH:29]=[N:30]1)[CH3:34]

참가 물질

7

반응물 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 67237978Methyl 6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)nicotinate

생성물 1

HCID 86654724tert-Butyl (1S,2R)-2-(4-(1-ethyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate수율 86%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매2회HCID 6344Dichloromethane용매

실험 절차

To a flask containing methyl 6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexyl-amino)-4-cyano-2-(1-ethyl-1H-pyrazol-4-yl)nicotinate (62 mg, 0.132 mmol) in MeOH (2 mL) was added HOAc (1 mL) to give a yellow solution. Palladium on carbon was added (14.08 mg, 0.132 mmol). The flask was evacuated and filled with H2 three times, after which the mixture was stirred vigorously at RT under a H2 atmosphere overnight. The mixture was filtered through Celite, and the solvent was removed in vacuo to give a residue, which was dissolved in DCM (10 mL) and MeOH (10 mL). Potassium carbonate was added and the mixture was stirred for 5 h. The solids were filtered out and the filtrate concentrated to give the title compound (50 mg, 86%). [M+H] calc'd for C23H32N6O3, 441; found, 441.

후처리

  1. customto give a yellow solution
  2. customThe flask was evacuated
  3. additionfilled with H2 three times
  4. filtrationThe mixture was filtered through Celite
  5. customthe solvent was removed in vacuo
  6. customto give a residue, which
  7. stirringthe mixture was stirred for 5 h
  8. filtrationThe solids were filtered out
  9. concentrationthe filtrate concentrated

출처 및 근거

ORD 기록
ord-c39d3124679046809847a0c0b4c2fe9d
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108970B2

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