Water → Tert-butyl(5-{[2-(cyclopropylcarbonyl)amino[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-fluorophenyl)carbamate

HRID 1800548ノート

反応式

HRID 1800548 の反応式
[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[N:20]=[C:19]3[S:21][C:22]([NH2:24])=[N:23][C:18]3=[CH:17][CH:16]=2)[CH:11]=[CH:10][C:9]=1[F:25])([CH3:4])([CH3:3])[CH3:2].[CH:27]1([C:30](Cl)=[O:31])[CH2:29][CH2:28]1.O>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[N:20]=[C:19]3[S:21][C:22]([NH:24][C:30]([CH:27]4[CH2:29][CH2:28]4)=[O:31])=[N:23][C:18]3=[CH:17][CH:16]=2)[CH:11]=[CH:10][C:9]=1[F:25])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 962WaterHCID 77637Cyclopropanecarbonyl chlorideHCID 86657972Tert-butyl {5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-2-fluorophenyl}carbamate

生成物 1

HCID 70688667Tert-butyl(5-{[2-(cyclopropylcarbonyl)amino[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-fluorophenyl)carbamate収率 59%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

実験手順

To a solution of tert-butyl{5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-2-fluorophenyl}carbamate (1.13 g, 3.0 mmol) and N,N-dimethylpyridine-4-amine (1.22 g, 10 mmol) in pyridine (10 mL) was added dropwise cyclopropanecarbonyl chloride (1.05 g, 10 mmol) under ice-cooling, and the mixture was stirred at room temperature overnight. To the reaction mixture was added water (200 mL), and the mixture was extracted with ethyl acetate (100 mL×2). The ethyl acetate layers were combined, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was triturated with diethyl ether to give the title compound (0.78 g, 59%) as a pale-yellow amorphous.

後処理

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate (100 mL×2)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was triturated with diethyl ether

出典と根拠

ORDレコード
ord-f86c661e3fec409c8fb03c9df8e49e72
出典データセット
uspto-grants-2013_01
特許番号
US08344135B2

反応ノート

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