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Sodium → N-(2-Hydroxymethylthiazolo[5,4-b]pyrid-6-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide

HRID 2069526
ノート
印刷プレビュー

反応式

HRID 2069526 の反応式
[Na].CC(C)(C)C([O:6][CH2:7][C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][C:13]([NH:17][C:18]([C:20]1[N:21]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=3)[C:22]3[C:27]([CH:28]=1)=[CH:26][C:25]([F:29])=[CH:24][CH:23]=3)=[O:19])=[CH:12][N:11]=2)=O>CO>[OH:6][CH2:7][C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][C:13]([NH:17][C:18]([C:20]1[N:21]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=3)[C:22]3[C:27]([CH:28]=1)=[CH:26][C:25]([F:29])=[CH:24][CH:23]=3)=[O:19])=[CH:12][N:11]=2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 5360545SodiumHCID 66888934HCID 66888934、化合物2 回

生成物 1

HCID 44181666N-(2-Hydroxymethylthiazolo[5,4-b]pyrid-6-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide収率 55.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
20 °C

実験手順

50 mg (2.03 mmol) of sodium are added to 8 mL of methanol with stirring at 20° C. After 15 minutes, a solution of 0.15 g (0.28 mmol) of [6-[[[5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indol-2-yl]carbonyl]amino]thiazolo[5,4-b]pyrid-2-yl]methyl 2,2-dimethylpropanoate (Compound 13), prepared in step 4.3, in 16 mL of methanol is added. Stirring is continued for 15 minutes at 20° C., and the reaction mixture is then concentrated under reduced pressure and taken up in 200 mL of molar ammonium chloride solution. The aqueous phase is extracted three times with 50 mL of ethyl acetate. The organic phases are combined, washed with 50 mL of saturated sodium chloride solution and then dried over sodium sulfate and concentrated under reduced pressure. The product thus obtained is purified on a column of silica, eluting with a mixture of dichloromethane and methanol. 70 mg of the expected product are thus isolated.

後処理

  1. additionis added
  2. stirringStirring
  3. waitis continued for 15 minutes at 20° C.
  4. concentrationthe reaction mixture is then concentrated under reduced pressure
  5. extractionThe aqueous phase is extracted three times with 50 mL of ethyl acetate
  6. washwashed with 50 mL of saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe product thus obtained
  10. customis purified on a column of silica
  11. washeluting with a mixture of dichloromethane and methanol

出典と根拠

ORDレコード
ord-c397f6602dac48dcb40a7624ce67402b
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08299114B2

反応ノート

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