Hydrogen Peroxide → 4-Hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (5-methanesulfonyl-7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide

HRID 550849ノート

反応式

HRID 550849 の反応式
[CH3:1][O:2][C:3]1[C:4]2[N:13]=[C:12]([NH:14][C:15]([N:17]3[CH2:22][CH2:21][C:20]([OH:33])([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=4)[CH2:19][CH2:18]3)=[O:16])[S:11][C:5]=2[N:6]=[C:7]([S:9][CH3:10])[N:8]=1.OO.[OH2:36].C[OH:38]>[O-][W]([O-])(=O)=O.[Na+].[Na+]>[CH3:10][S:9]([C:7]1[N:8]=[C:3]([O:2][CH3:1])[C:4]2[N:13]=[C:12]([NH:14][C:15]([N:17]3[CH2:22][CH2:21][C:20]([OH:33])([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:32])[F:31])[CH:24]=4)[CH2:19][CH2:18]3)=[O:16])[S:11][C:5]=2[N:6]=1)(=[O:38])=[O:36]

参加物

6

反応物 4

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 962WaterHCID 590119534-Hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (7-methoxy-5-methylsulfanyl-thiazolo[5,4-d]pyrimidin-2-yl)-amide

生成物 1

HCID 248306134-Hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (5-methanesulfonyl-7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide収率 63%

試薬・触媒・溶媒 1

HCID 26052Sodium tungstate触媒

実験手順

A magnetically stirred mixture of 4-hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (7-methoxy-5-methylsulfanyl-thiazolo[5,4-d]pyrimidin-2-yl)-amide (375 mg, 0.75 mmol) in methanol (20 mL) was cooled in an ice water bath and treated with sodium tungstate dihyrate (135 mg, 0.04 mmol) followed by hydrogen peroxide (30% solution, 10 mL) The reaction mixture was warmed to room temperature and stirred for 2 h. The reaction was then poured into water and extracted with methylene chloride. The organics were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated in vacuo to afford 4-hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (5-methanesulfonyl-7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide (251 mg, 63%) as a red solid. LRMS for C20H20F3N5O5S2 (M+H)+ at m/z=499. The NMR spectrum obtained on the sample is compatible with its structure.

後処理

  1. temperaturewas cooled in an ice water bath
  2. extractionextracted with methylene chloride
  3. washThe organics were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-9ce5796a435344a59dd63287bea523c9
出典データセット
uspto-grants-2011_05
特許番号
US07947692B2

反応ノート

読み込み中…