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

HRID 402684

反応式

HRID 402684 の反応式
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.[NH2:35][CH2:36][CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.[NH:43]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][N:50]=2)[C:45]([CH:52]=O)=[CH:44]1.N1CCCCC1>CC(O)C>[NH:43]1[C:51]2=[N:50][CH:49]=[CH:48][CH:47]=[C:46]2[C:45]([CH:52]=[C:7]2[O:6][C:5]([NH:35][CH2:36][CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)=[C:9]([C:10]([O:12][CH:13]([CH3:14])[CH3:15])=[O:11])[C:8]2=[O:16])=[CH:44]1

参加物

8

反応物 6

HCID 6577Chloroacetyl chlorideHCID 8082PiperidineHCID 76688CyclohexanemethylamineHCID 83223Diisopropyl malonateHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 51050080Isopropyl 2-isopropoxy-4-oxo-4,5-dihydrofuran-3-carboxylate

生成物 1

HCID 178459409propan-2-yl 2-(cyclohexylmethylamino)-4-oxo-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylidene)furan-3-carboxylate収率 20%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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 aminomethylcyclohexane (0.063 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 (0.036 g, y. 19%).

後処理

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

出典と根拠

ORDレコード
ord-20dde74e66a94bd095fda331e0a36e7d
出典データセット
uspto-grants-2014_06
特許番号
US08742113B2

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