Lithium Hydroxide → Lithium 2-(2-(2-(2-((4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-2-methoxyphenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetate

HRID 705726ノート

反応式

HRID 705726 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:33]2[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]2)[CH:6]=[CH:7][C:8]=1[NH:9][C:10]1[N:15]=[C:14]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH2:24][C:25]([O:27]C)=[O:26])[C:13]([C:29]([F:32])([F:31])[F:30])=[CH:12][N:11]=1.[OH-].[Li+:47]>O1CCCC1.CO.O>[C:42]([O:41][C:39]([N:36]1[CH2:37][CH2:38][N:33]([C:5]2[CH:6]=[CH:7][C:8]([NH:9][C:10]3[N:15]=[C:14]([CH2:16][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[CH2:24][C:25]([O-:27])=[O:26])[C:13]([C:29]([F:31])([F:32])[F:30])=[CH:12][N:11]=3)=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:34][CH2:35]1)=[O:40])([CH3:45])([CH3:44])[CH3:43].[Li+:47]

参加物

6

反応物 2

HCID 3939Lithium HydroxideHCID 71225693tert-Butyl 4-(3-methoxy-4-((4-(2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperazine-1-carboxylate

生成物 1

HCID 71225535Lithium 2-(2-(2-(2-((4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-2-methoxyphenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetate

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of tert-butyl 4-(3-methoxy-4-((4-(2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperazine-1-carboxylate (I6) (0.360 g, 0.572 mmol) in tetrahydrofuran (17 mL), methanol (3 mL) and water (5 mL) was added lithium hydroxide (0.042 g, 1.77 mmol) and the resulting mixture was stirred at room temperature for 20 hours. The reaction volatiles were evaporated in vacuo and the resulting residue was diluted with ethyl acetate and saturated aqueous sodium hydrogen carbonate. The aqueous phase was extracted with ethyl acetate (3×20 mL) and the combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate (20 mL), dried (magnesium sulfate), filtered, evaporated in vacuo and dried to give the title compound (I7) (0.356 g, 100%) as a yellow foam; 1H NMR (300 MHz, CDCl3) δ 1.48 (s, 9H), 2.96-3.06 (m, 8H) 3.56-3.62 (m, 6H), 3.77 (s, 3H), 6.47-6.51 (m, 2H), 7.00-7.11 (m, 2H), 8.00 (brs, 2H) and 8.43 (s, 1H). LCMS Method B: rt 9.00 min; m/z 616.4 [M+H]+.

後処理

  1. customThe reaction volatiles
  2. customwere evaporated in vacuo
  3. additionthe resulting residue was diluted with ethyl acetate and saturated aqueous sodium hydrogen carbonate
  4. extractionThe aqueous phase was extracted with ethyl acetate (3×20 mL)
  5. washthe combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate (20 mL)
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customdried

出典と根拠

ORDレコード
ord-3e8f721d3974492682d20aae1ff97aff
出典データセット
uspto-grants-2015_11
特許番号
US09174946B2

反応ノート

読み込み中…