Isopropanol → 3-(4-((Benzyloxycarbonylamino)methyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate

HRID 216070노트

반응식

HRID 216070 반응식
[CH3:1][N:2]([CH3:33])[C:3](=[O:32])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([CH2:20][NH:21][C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[O:13])[CH:6]=1.Cl[C:35]1[C:36]2[C:43]([CH3:44])=[CH:42][NH:41][C:37]=2[N:38]=[CH:39][N:40]=1.C(N(CC)C(C)C)(C)C.C(O)(C)C>C(Cl)Cl>[CH3:1][N:2]([CH3:33])[C:3](=[O:32])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([CH2:20][NH:21][C:22]([O:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:23])[CH2:19][CH2:18][N:17]([C:35]3[C:36]4[C:43]([CH3:44])=[CH:42][NH:41][C:37]=4[N:38]=[CH:39][N:40]=3)[CH2:16][CH2:15]2)=[O:13])[CH:6]=1

참가 물질

6

반응물 4

HCID 3776IsopropanolHCID 81531DiisopropylethylamineHCID 148092824-Chloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidineHCID 670367573-(4-((Benzyloxycarbonylamino)methyl)piperidine-4-carboxamido)phenyl dimethylcarbamate

생성물 1

HCID 579202083-(4-((Benzyloxycarbonylamino)methyl)-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate수율 54%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
120 °C

실험 절차

3-(4-((Benzyloxycarbonylamino)methyl)piperidine-4-carboxamido)phenyl dimethylcarbamate (0.216 g, 0.441 mmol) from step D, 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (0.073 g, 0.441 mmol), N,N-diisopropylethylamine (0.230 mL, 1.32 mmol), and isopropanol (5 mL) were combined and heated at 120° C. overnight in a pressure vessel. The crude reaction was diluted with CH2Cl2 and washed with H2O and brine, dried over MgSO4, and concentrated under vacuum. The residue was purified by silica gel chromatography (MeOH:CH2Cl2 gradient) to give the title compound in 54% yield.

후처리

  1. customThe crude reaction
  2. washwashed with H2O and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica gel chromatography (MeOH:CH2Cl2 gradient)

출처 및 근거

ORD 기록
ord-36b1dc678aa849519aeafa90381f5368
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193202B2

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