Chloroacetyl chloride → propan-2-yl 2-(cyclohexylamino)-4-oxo-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylidene)furan-3-carboxylate

HRID 402683

반응식

HRID 402683 반응식
C(O[C:5]1[O:6][CH2:7][C:8](=[O:16])[C:9]=1[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])(C)C.C(OC(C)C)(=O)CC(OC(C)C)=O.ClCC(Cl)=O.[CH:35]1([NH2:41])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.[NH:42]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][N:49]=2)[C:44]([CH:51]=O)=[CH:43]1.N1CCCCC1>CC(O)C>[NH:42]1[C:50]2=[N:49][CH:48]=[CH:47][CH:46]=[C:45]2[C:44]([CH:51]=[C:7]2[O:6][C:5]([NH:41][CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)=[C:9]([C:10]([O:12][CH:13]([CH3:14])[CH3:15])=[O:11])[C:8]2=[O:16])=[CH:43]1

참가 물질

8

반응물 6

HCID 6577Chloroacetyl chlorideHCID 7965CyclohexylamineHCID 8082PiperidineHCID 83223Diisopropyl malonateHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 51050080Isopropyl 2-isopropoxy-4-oxo-4,5-dihydrofuran-3-carboxylate

생성물 1

HCID 178459408propan-2-yl 2-(cyclohexylamino)-4-oxo-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylidene)furan-3-carboxylate수율 4.5%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A solution of isopropyl 2-isopropoxy-4-oxo-4,5-dihydrofuran-3-carboxylate (0.10 g, 0.44 mmol) which similarly prepared according to the procedure described in the Example 74, Third step using diisopropyl malonate and chloroacetyl chloride, and cyclohexylamine (0.055 mL, 0.48 mmol) in 2-propanol (2.0 mL) was stirred at ambient temperature for 14 h. To this reaction mixture, 7-azaindole-3-carboxaldehyde (0.065 g, 0.44 mmol) and piperidine (0.0044 mL, 0.044 mmol) were added then the mixture was refluxed for further 8 days. Cooled to ambient temperature, the reaction mixture was purified by preparative HPLC to afford the titled compound as solid (0.0079 g, y. 4%).

후처리

  1. temperaturethe mixture was refluxed for further 8 days
  2. temperatureCooled to ambient temperature
  3. customthe reaction mixture was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-486f09d95e5c4967901e330da4bade40
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742113B2

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