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 1779015Notes

Reaction equation

HRID 1779015 reaction equation
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]

Participants

5

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-cbfe8206618b44b69c87de8e00994969
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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