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

HRID 550836
ノート
印刷プレビュー

反応式

HRID 550836 の反応式
Cl[C:2]1[C:7]([NH:8][C:9]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][C:17]([OH:30])([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[CH2:16][CH2:15]2)=[O:13])=[S:10])=[C:6]([O:31][CH3:32])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].C(OCC)(=O)C.CCCCCC>C1COCC1>[CH3:32][O:31][C:6]1[CH:5]=[CH:4][N:3]=[C:2]2[S:10][C:9]([NH:11][C:12]([N:14]3[CH2:19][CH2:18][C:17]([OH:30])([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=4)[CH2:16][CH2:15]3)=[O:13])=[N:8][C:7]=12
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 21226206Ethyl acetate hexaneHCID 590119851-(2-Chloro-4-methoxy-pyridin-3-yl)-3-[4-hydroxy-4-(3-trifluoromethylphenyl)-piperidine-1-carbonyl]-thiourea

生成物 1

HCID 248306154-Hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (7-methoxy-thiazolo[5,4-b]pyridine-2-yl)-amide収率 22%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a magnetically stirred mixture of 1-(2-Chloro-4-methoxy-pyridin-3-yl)-3-[4-hydroxy-4-(3-trifluoromethylphenyl)-piperidine-1-carbonyl]-thiourea (100 mg, 0.20 mmol) in THF (10 mL) was added sodium hydride (10 mg, 0.25 mmole, 60% dispersion in mineral oil). The reaction is stirred at reflux overnight. TLC (80% ethyl acetate/hexane) indicated complete consumption of starting material. The reaction was poured into water and the aqueous layer was extracted with ethyl acetate. The resulting organic layers were washed with 2N HCl (2×) and saturated sodium chloride solution and then dried over magnesium sulfate. Purification by flash chromatography gave 4-Hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (7-methoxy-thiazolo[5,4-b]pyridine-2-yl)-amide (20 mg, 0.04 mmole, 22% yield) as a light yellow solid. (LRMS for C20H19F3N4O3S (M+H)+ at m/z=452.

後処理

  1. temperatureat reflux overnight
  2. customconsumption of starting material
  3. additionThe reaction was poured into water
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe resulting organic layers were washed with 2N HCl (2×) and saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customPurification by flash chromatography

出典と根拠

ORDレコード
ord-00c1831b864f4f5a96cc85bcc69d66cb
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

読み込み中…

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