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

HRID 550848
ノート
印刷プレビュー

反応式

HRID 550848 の反応式
[CH3:1][O:2][C:3]1[C:4]2[N:13]=[C:12]([NH2:14])[S:11][C:5]=2[N:6]=[C:7]([S:9][CH3:10])[N:8]=1.[H-].[Na+].C(N(CC)C(C)C)(C)C.[OH:26][C:27]1([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([F:45])([F:44])[F:43])[CH:37]=2)[CH2:32][CH2:31][N:30]([C:33](Cl)=[O:34])[CH2:29][CH2:28]1>O1CCCC1>[CH3:1][O:2][C:3]1[C:4]2[N:13]=[C:12]([NH:14][C:33]([N:30]3[CH2:29][CH2:28][C:27]([OH:26])([C:36]4[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([F:44])([F:43])[F:45])[CH:37]=4)[CH2:32][CH2:31]3)=[O:34])[S:11][C:5]=2[N:6]=[C:7]([S:9][CH3:10])[N:8]=1
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

6

反応物 4

HCID 24758Sodium hydrideHCID 81531DiisopropylethylamineHCID 590119344-Hydroxy4-[3-(trifluoromethyl)phenyl]piperidine-1-carbonyl chlorideHCID 590119397-Methoxy-5-methylsulfanyl-thiazolo[5,4-d]pyrimidin-2-ylamine

生成物 1

HCID 590119534-Hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (7-methoxy-5-methylsulfanyl-thiazolo[5,4-d]pyrimidin-2-yl)-amide
収率 34.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A magnetically stirred mixture of 7-Methoxy-5-methylsulfanyl-thiazolo[5,4-d]pyrimidin-2-ylamine (500 mg, 2.19 mmol) in tetrahydrofuran (20 mL) under a nitrogen atmosphere at 25° C. was treated with sodium hydride (60% suspension in mineral oil, 265 mg, 6.58 mmol). The reaction mixture was stirred at 50° C. for 1 h. At this time, the reaction was cooled to room temperature and was treated with N,N-diisopropylethylamine (850 mg, 6.58 mmol) and 4-hydroxy-4-[3-(trifluoromethyl)phenyl]piperidine-1-carbonyl chloride (810 mg, 2.63 mmol). The reaction mixture was stirred at room temperature for 3 d. At this time, the reaction was concentrated in vacuo, poured into water and extracted with ethyl acetate. The organics were washed with a 2N aqueous hydrochloric acid solution and a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 98:2 methylene chloride/methanol) afforded 4-hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (7-methoxy-5-methylsulfanyl-thiazolo[5,4-d]pyrimidin-2-yl)-amide (375 mg, 34%) as a red solid. LRMS for C20H20F3N5O3S2 (M+H)+ at m/z=499. The NMR spectrum obtained on the sample is compatible with its structure.

後処理

  1. temperatureAt this time, the reaction was cooled to room temperature
  2. stirringThe reaction mixture was stirred at room temperature for 3 d
  3. concentrationAt this time, the reaction was concentrated in vacuo
  4. additionpoured into water
  5. extractionextracted with ethyl acetate
  6. washThe organics were washed with a 2N aqueous hydrochloric acid solution
  7. dry with materiala saturated aqueous sodium chloride solution, dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ea604829a2ff49f19987e54bfe88b4bc
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07947692B2

反応ノート

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