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

HRID 1800629ノート

反応式

HRID 1800629 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[CH:20]=[CH:21][C:22]([Cl:32])=[C:23]([NH:25]C(=O)C(F)(F)F)[CH:24]=1)[N:12]=2)(=[O:7])[CH3:6]>C(O)C.C(OCC)(=O)C>[NH2:25][C:23]1[CH:24]=[C:19]([CH:20]=[CH:21][C:22]=1[Cl:32])[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 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86646052N-(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-chlorophenyl)-2,2,2-trifluoroacetamide

生成物 1

HCID 86646053N-[5-(3-amino-4-chlorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]acetamide収率 50%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Sodium borohydride (2.45 g, 64.8 mmol) was suspended in ethanol (43 mL), and methanol (29 mL) was slowly added. To the obtained reaction mixture was added N-(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-chlorophenyl)-2,2,2-trifluoroacetamide (1.5 g, 3.48 mmol) powder in small portions under cooling in a water bath, and then, the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with ethyl acetate (100 mL), and partitioned with water (50 mL), and the organic layer was concentrated under reduced pressure. The residue was diluted with ethyl acetate (80 mL), and washed with saturated brine (80 mL). The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=40/60→100/0), and triturated with diisopropyl ether to give the title compound (0.58 g, 50%) as a white solid.

後処理

  1. customTo the obtained reaction mixture
  2. temperatureunder cooling in a water bath
  3. custompartitioned with water (50 mL)
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. additionThe residue was diluted with ethyl acetate (80 mL)
  6. washwashed with saturated brine (80 mL)
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=40/60→100/0)
  10. customtriturated with diisopropyl ether

出典と根拠

ORDレコード
ord-204ed57e169842cd9ebc71dd3dc4e892
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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