Methanol → N-[5-(5-amino-2-chloro-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]acetamide

HRID 1800543ノート

反応式

HRID 1800543 の反応式
[BH4-].[Na+].CO.[C:5]([NH:8][C:9]1[S:10][C:11]2[C:16]([N:17]=1)=[CH:15][CH:14]=[C:13]([O:18][C:19]1[C:20]([Cl:33])=[CH:21][C:22]([F:32])=[C:23]([NH:25]C(=O)C(F)(F)F)[CH:24]=1)[N:12]=2)(=[O:7])[CH3:6].O>C(O)C>[NH2:25][C:23]1[C:22]([F:32])=[CH:21][C:20]([Cl:33])=[C:19]([CH:24]=1)[O:18][C:13]1[N:12]=[C:11]2[S:10][C:9]([NH:8][C:5](=[O:7])[CH3:6])=[N:17][C:16]2=[CH:15][CH:14]=1

参加物

6

反応物 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 86646020N-(5-{[2-(acetylamino) [1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-4-chloro-2-fluorophenyl)-2,2,2-trifluoroacetamide

生成物 1

HCID 86646021N-[5-(5-amino-2-chloro-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]acetamide収率 192.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of sodium borohydride (3.38 g, 100 mmol) in ethanol (60 mL) was added dropwise methanol (40 mL) under ice-cooling, and N-(5-{[2-(acetylamino) [1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-4-chloro-2-fluorophenyl)-2,2,2-trifluoroacetamide (2.16 g, 4.81 mmol) was added in portions thereto under ice-cooling. The reaction mixture was stirred at room temperature for 1 hr, and poured into water (400 mL), and the mixture was extracted with ethyl acetate (200 mL×2). The ethyl acetate layers were combined, and dried over anhydrous sodium 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 (3.26 g, 68%) as white powder crystals.

後処理

  1. temperaturecooling
  2. temperatureunder ice-cooling
  3. extractionthe mixture was extracted with ethyl acetate (200 mL×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. washThe obtained residue was washed with diethyl ether
  8. filtrationcollected by filtration
  9. customdried under reduced pressure

出典と根拠

ORDレコード
ord-69ebd5c52a8748cbb9c08a15841369c7
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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