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

HRID 1473116Notes

Reaction equation

HRID 1473116 reaction equation
C[O:2][C:3](=[O:44])[CH2:4][C:5]1[CH:43]=[CH:42][CH:41]=[CH:40][C:6]=1[CH2:7][CH2:8][C:9]1[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][N:12]=[C:11]([NH:19][C:20]2[CH:39]=[CH:38][C:23]([CH2:24][N:25]3[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]3)=[CH:22][CH:21]=2)[N:10]=1.O.[OH-].[Li+:47]>C1COCC1.O>[C:34]([O:33][C:31]([N:28]1[CH2:27][CH2:26][N:25]([CH2:24][C:23]2[CH:38]=[CH:39][C:20]([NH:19][C:11]3[N:10]=[C:9]([CH2:8][CH2:7][C:6]4[CH:40]=[CH:41][CH:42]=[CH:43][C:5]=4[CH2:4][C:3]([O-:44])=[O:2])[C:14]([C:15]([F:16])([F:17])[F:18])=[CH:13][N:12]=3)=[CH:21][CH:22]=2)[CH2:30][CH2:29]1)=[O:32])([CH3:37])([CH3:35])[CH3:36].[Li+:47]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 71229652tert-Butyl 4-(4-((4-(2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzyl)piperazine-1-carboxylate

Product 1

HCID 68282975Lithium 2-(2-(2-(2-((4-((4-(tert-butoxycarbonyl)piperazin-1-yl)methyl)phenyl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 4-(4-((4-(2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzyl)piperazine-1-carboxylate (I96) (120 mg, 0.196 mmol) was dissolved in THF (4 mL), and a solution of lithium hydroxide hydrate (25 mg, 0.59 mmol) in water (1 mL) was added. The mixture was stirred at room temperature for 18 hours then concentrated and the residue evaporated twice from toluene to give the title compound (I97) as a tan solid which was used without purification. LCMS Method C: rt 5.17 min; m/z 600.2 [M−Li+2H]+; 544.1 [M−tBu−Li+3H]+; m/z 598.2 [M−Li]−.

Workup

  1. concentrationthen concentrated
  2. customthe residue evaporated twice from toluene

Sources & evidence

ORD record
ord-ed3be742075d4ff1a38720719a494f0c
Source dataset
uspto-grants-2015_04
Patent number
US09012461B2

Reaction notes

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