Lithium hydroxide, monohydrate → HCID 86712736, compound

HRID 1779107Notes

Reaction equation

HRID 1779107 reaction equation
C[O:2][C:3](=[O:42])[CH2:4][C:5]1[CH:41]=[CH:40][CH:39]=[CH:38][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:21]=[N:22][N:23]([CH: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:24]=2)[N:10]=1.O[Li].O>C1COCC1.O.C(Cl)Cl>[C:34]([O:33][C:31]([N:28]1[CH2:27][CH2:26][CH:25]([N:23]2[CH:24]=[C:20]([NH:19][C:11]3[N:10]=[C:9]([CH2:8][CH2:7][C:6]4[CH:38]=[CH:39][CH:40]=[CH:41][C:5]=4[CH2:4][C:3]([OH:42])=[O:2])[C:14]([C:15]([F:16])([F:17])[F:18])=[CH:13][N:12]=3)[CH:21]=[N:22]2)[CH2:30][CH2:29]1)=[O:32])([CH3:37])([CH3:35])[CH3:36]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86712734HCID 86712734, compound

Product 1

HCID 86712736HCID 86712736, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of tert-butyl 4-(4-((4-(2-(2-methoxy-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)piperidine-1-carboxylate (A135) (300 mg, 0.510 mmol) and LiOH.H2O (855 mg, 20.4 mmol) in THF (20 mL) and H2O (1 mL) was stirred at 40° C. overnight. The mixture was diluted with DCM (50 mL) and water (50 mL) and the aqueous layer was extracted with EtOAc (2×50 mL). The combined washings were dried (Na2SO4) and the volatiles were removed in vacuo to yield the title compound (A136) as a yellow oil (270 mg, 92%). LCMS-A: rt 6.679 min; m/z 575.2 [M+H]+.

Workup

  1. extractionthe aqueous layer was extracted with EtOAc (2×50 mL)
  2. dry with materialThe combined washings were dried (Na2SO4)
  3. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-c7bb5b1037fb467e96a6cd01adc048fe
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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