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

HRID 1779015노트

반응식

HRID 1779015 반응식
O[Li:2].O.[F:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:43][C:44]([O:46]C)=[O:45])=[C:9]([CH:42]=1)[CH2:10][CH2:11][C:12]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][N:15]=[C:14]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([CH:29]3[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]3)=[CH:25][CH:24]=2)[N:13]=1>O.C1COCC1>[C:38]([O:37][C:35]([N:32]1[CH2:31][CH2:30][CH:29]([C:26]2[CH:25]=[CH:24][C:23]([NH:22][C:14]3[N:13]=[C:12]([CH2:11][CH2:10][C:9]4[CH:42]=[C:5]([F:4])[CH:6]=[CH:7][C:8]=4[CH2:43][C:44]([O-:46])=[O:45])[C:17]([C:18]([F:19])([F:20])[F:21])=[CH:16][N:15]=3)=[CH:28][CH:27]=2)[CH2:34][CH2:33]1)=[O:36])([CH3:41])([CH3:39])[CH3:40].[Li+:2]

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 86712666tert-Butyl 4-(4-((4-(5-fluoro-2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

생성물 1

HCID 86712667Lithium 2-(2-(2-(2-((4-(1-(tert-butoxycarbonyl)piperidin-4-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)-4-fluorophenyl)acetate

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
40 °C

실험 절차

LiOH.H2O (0.063 g, 1.5 mmol) was added to a stirred solution of tert-butyl 4-(4-((4-(5-fluoro-2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (A52) (0.092 g, 0.15 mmol) in H2O (0.5 mL) and THF (5 mL) and the resulting mixture heated at 40° C. overnight. The volatiles were removed in vacuo and the residue was taken up in DCM (50 mL). The resulting solution was washed with saturated aqueous Na2CO3 (25 mL) then the aqueous phase was then extracted with DCM (2×25 mL). The organic layers were combined, dried over MgSO4 and the volatiles were removed in vacuo to yield the title compound A53 (0.089 g, 98%); LCMS-A: rt 6.596 min; m/z 603 [(M-Li)+H]+.

후처리

  1. customThe volatiles were removed in vacuo
  2. washThe resulting solution was washed with saturated aqueous Na2CO3 (25 mL)
  3. extractionthe aqueous phase was then extracted with DCM (2×25 mL)
  4. dry with materialdried over MgSO4
  5. customthe volatiles were removed in vacuo

출처 및 근거

ORD 기록
ord-cbfe8206618b44b69c87de8e00994969
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266864B2

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