Lithium hydroxide, monohydrate → Lithium 2-(4-(2-(2-((4-(1-(tert-butoxycarbonyl)piperidin-4-yl)phenyl)amino)-5-(trifluoro-methyl)pyrimidin-4-yl)ethyl)pyrimidin-5-yl)acetate

HRID 1473134ノート

反応式

HRID 1473134 の反応式
O[Li:2].O.C([O:6][C:7](=[O:47])[CH2:8][C:9]1[C:10]([CH2:15][CH2:16][C:17]2[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][N:20]=[C:19]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([CH:34]4[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]4)=[CH:30][CH:29]=3)[N:18]=2)=[N:11][CH:12]=[N:13][CH:14]=1)C>C1COCC1.O.CO>[C:43]([O:42][C:40]([N:37]1[CH2:36][CH2:35][CH:34]([C:31]2[CH:30]=[CH:29][C:28]([NH:27][C:19]3[N:18]=[C:17]([CH2:16][CH2:15][C:10]4[C:9]([CH2:8][C:7]([O-:47])=[O:6])=[CH:14][N:13]=[CH:12][N:11]=4)[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][N:20]=3)=[CH:33][CH:32]=2)[CH2:39][CH2:38]1)=[O:41])([CH3:46])([CH3:44])[CH3:45].[Li+:2]

参加物

6

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 71209322tert-Butyl 4-(4-((4-(2-(5-(2-ethoxy-2-oxoethyl)pyrimidin-4-yl)ethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

生成物 1

HCID 71209343Lithium 2-(4-(2-(2-((4-(1-(tert-butoxycarbonyl)piperidin-4-yl)phenyl)amino)-5-(trifluoro-methyl)pyrimidin-4-yl)ethyl)pyrimidin-5-yl)acetate収率 103.9%

試薬・触媒・溶媒 3

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

実験手順

LiOH.H2O (0.020 g, 0.468 mmol) was added to a solution of tert-butyl 4-(4-((4-(2-(5-(2-ethoxy-2-oxoethyl)pyrimidin-4-yl)ethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (I112) (0.096 g, 0.156 mmol) in THF (7 mL), water (1.5 mL) and methanol (1 mL) and the resulting mixture was allowed to stir at room temperature for 18 hours. The volatiles were removed in vacuo and the residue was diluted with EtOAc (70 mL) and 2 M aqueous NaOH (80 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×70 mL), the combined organics were washed with brine (70 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give the title compound (I113) (0.096 g, quantitative) as a pale yellow solid. LCMS Method C: rt 6.19 min; m/z 587.1 [M+H]+.

後処理

  1. customThe volatiles were removed in vacuo
  2. additionthe residue was diluted with EtOAc (70 mL) and 2 M aqueous NaOH (80 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×70 mL)
  5. washthe combined organics were washed with brine (70 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-464b15f14aa641feb3417ddc2e7cea19
出典データセット
uspto-grants-2015_04
特許番号
US09012461B2

反応ノート

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