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 1473134노트

반응식

HRID 1473134 반응식
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]

참가 물질

6

반응물 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

생성물 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)acetate수율 103.9%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-464b15f14aa641feb3417ddc2e7cea19
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012461B2

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