Lithium hydroxide, monohydrate → 2-(2-(2-(2-((4-(1-(tert-Butoxycarbonyl)piperidin-3-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyridin-3-yl)acetic acid

HRID 1485287Notes

Reaction equation

HRID 1485287 reaction equation
C[O:2][C:3](=[O:43])[CH2:4][C:5]1[C:6]([CH2:11][CH2:12][C:13]2[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([CH:30]4[CH2:35][CH2:34][CH2:33][N:32]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:31]4)=[CH:26][CH:25]=3)[N:14]=2)=[N:7][CH:8]=[CH:9][CH:10]=1.O.[OH-].[Li+]>C1COCC1.O.CO>[C:39]([O:38][C:36]([N:32]1[CH2:33][CH2:34][CH2:35][CH:30]([C:27]2[CH:28]=[CH:29][C:24]([NH:23][C:15]3[N:14]=[C:13]([CH2:12][CH2:11][C:6]4[C:5]([CH2:4][C:3]([OH:43])=[O:2])=[CH:10][CH:9]=[CH:8][N:7]=4)[C:18]([C:19]([F:20])([F:21])[F:22])=[CH:17][N:16]=3)=[CH:25][CH:26]=2)[CH2:31]1)=[O:37])([CH3:42])([CH3:40])[CH3:41]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 71209105tert-Butyl 3-(4-((4-(2-(3-(2-methoxy-2-oxoethyl)pyridin-2-yl)ethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate

Product 1

HCID 682828572-(2-(2-(2-((4-(1-(tert-Butoxycarbonyl)piperidin-3-yl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)pyridin-3-yl)acetic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 3-(4-((4-(2-(3-(2-methoxy-2-oxoethyl)pyridin-2-yl)ethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (I148) (0.030 g, 0.050 mmol) in THF (7 mL), water (1.5 mL) and MeOH (1 mL) was added lithium hydroxide monohydrate (0.020 g, 0.48 mmol). The reaction mixture was stirred at room temperature for 17 hours then the volatiles were removed in vacuo and the residue was partitioned between ethyl acetate (10 mL) and saturated aqueous sodium hydrogen carbonate (10 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with brine (10 mL), dried (MgSO4) then the solvent removed in vacuo to give the title compound (I149) (0.029 g, 99%) as a white solid. LCMS Method C: rt 5.50 min, m/z=586.1 [M+H]+, 584.2 [M−H]−.

Workup

  1. customthe volatiles were removed in vacuo
  2. customthe residue was partitioned between ethyl acetate (10 mL) and saturated aqueous sodium hydrogen carbonate (10 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×10 mL)
  5. washThe combined organic layers were washed with brine (10 mL)
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-6c8af2bb421e40fd8ae486d1ce5b5b01
Source dataset
uspto-grants-2016_08
Patent number
US09421205B2

Reaction notes

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