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Tetrahydrofuran → 2-[3-(1,3-Thiazol-5-yl)-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl]propan-2-ol

HRID 410410
ノート
印刷プレビュー

反応式

HRID 410410 の反応式
[S:1]1[C:5]([C:6]2[CH:7]=[C:8]([CH:13]=[C:14]([NH:16][C:17]3[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][N:18]=3)[CH:15]=2)C(OC)=O)=[CH:4][N:3]=[CH:2]1.[CH2:27]1COCC1.C[Mg]Cl.C([O:38][CH2:39][CH3:40])(=O)C>>[S:1]1[C:5]([C:6]2[CH:7]=[C:8]([C:39]([OH:38])([CH3:40])[CH3:27])[CH:13]=[C:14]([NH:16][C:17]3[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][N:18]=3)[CH:15]=2)=[CH:4][N:3]=[CH:2]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

5

反応物 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 67262142Methyl 3-(1,3-thiazol-5-yl)-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}benzoateHCID 178418332HCID 178418332、化合物2 回

生成物 1

HCID 584564182-[3-(1,3-Thiazol-5-yl)-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl]propan-2-ol収率 74%

反応条件

温度
0 °C

実験手順

To a flask containing the product of Step 3 (254 mg, 0.67 mmol) was added THF (6.7 mL). The solution was cooled to 0° C. and then methylmagnesium chloride (3.0M in Et2O, 1.1 mL, 3.3 mmol) was added and the reaction was stirred for one hour. After one hour, more methylmagnesium chloride (3.0M in Et2O, 1.1 mL, 3.3 mmol) was added and the reaction was stirred for 30 minutes. The reaction was then diluted with ethyl acetate and carefully quenched with water and then diluted with water. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated. Flash chromatography was used for purification to yield 2-[3-(1,3-thiazol-5-yl)-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl]propan-2-ol (188 mg, 0.49 mmol, 74% yield). MS ESI: [M+H]+ m/z 381. 1H NMR (500 MHz, DMSO-d6) δ 10.26 (s, 1H), 9.07 (s, 1H), 8.82 (d, J=4.8, 1H), 8.20 (s, 1H), 8.03 (s, 1H), 7.79 (s, 1H), 7.45 (s, 1H), 7.28 (d, J=4.9, 1H), 5.12 (s, 1H), 1.46 (s, 6H).

後処理

  1. waitAfter one hour
  2. stirringthe reaction was stirred for 30 minutes
  3. customcarefully quenched with water
  4. additiondiluted with water
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customFlash chromatography was used for purification

出典と根拠

ORDレコード
ord-2b9311c483d34fe5ad0f1ea119bc5e0a
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08759366B2

反応ノート

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