Acetyl chloride → N-(5-{[2-(acetylamino) [1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-4-chloro-2-fluorophenyl)-2,2,2-trifluoroacetamide

HRID 1800542ノート

反応式

HRID 1800542 の反応式
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([O:11][C:12]1[C:13]([Cl:26])=[CH:14][C:15]([F:25])=[C:16]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH:17]=1)[N:5]=2.[C:27](Cl)(=[O:29])[CH3:28]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:27]([NH:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([O:11][C:12]1[C:13]([Cl:26])=[CH:14][C:15]([F:25])=[C:16]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:21])[F:22])[CH:17]=1)[N:5]=2)(=[O:29])[CH3:28]

参加物

5

反応物 2

HCID 6367Acetyl chlorideHCID 86646019N-{5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-chloro-2-fluorophenyl}-2,2,2-trifluoroacetamide

生成物 1

HCID 86646020N-(5-{[2-(acetylamino) [1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-4-chloro-2-fluorophenyl)-2,2,2-trifluoroacetamide収率 96.3%

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 N-{5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-chloro-2-fluorophenyl}-2,2,2-trifluoroacetamide (2.03 g, 5 mmol) and N,N-dimethylpyridine-4-amine (0.61 g, 5 mmol) in pyridine (10 mL) was added dropwise acetyl chloride (0.78 g, 10 mmol) under ice-cooling, and the mixture was stirred at room temperature for 3 hr. The reaction solution was concentrated under reduced pressure, and the residue was diluted with ethyl acetate (50 mL), washed with water (50 mL×2), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was washed with diethyl ether, collected by filtration, and dried under reduced pressure to give the title compound (2.16 g, 96%) as white powder crystals.

後処理

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate (50 mL)
  4. washwashed with water (50 mL×2)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. washThe obtained residue was washed with diethyl ether
  9. filtrationcollected by filtration
  10. customdried under reduced pressure

出典と根拠

ORDレコード
ord-3de9940c4b704b2b80b2bc2029ecf1f4
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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