Hydrochloric Acid → 4-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-3-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-4-oxo-butanoic acid

HRID 710667Notes

Reaction equation

HRID 710667 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][N:12]([C:17](=[O:35])[CH:18]([N:25]4[C:29]([CH3:30])=[CH:28][C:27]([C:31]([F:34])([F:33])[F:32])=[N:26]4)[CH2:19][C:20]([O:22]CC)=[O:21])[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.O[Li].O.C1COCC1.Cl>O.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][N:12]([C:17](=[O:35])[CH:18]([N:25]4[C:29]([CH3:30])=[CH:28][C:27]([C:31]([F:32])([F:34])[F:33])=[N:26]4)[CH2:19][C:20]([OH:22])=[O:21])[C:11]=3[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 86711682ethyl 4-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-3-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-4-oxo-butanoate

Product 1

HCID 867116834-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-3-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-4-oxo-butanoic acidYield 103.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 4-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-3-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-4-oxo-butanoate (0.030 g, 0.060 mmol), LiOH.H2O (0.020 g, 0.47 mmol), THF (0.4 mL), MeOH (0.4 mL) and H2O (0.2 mL) was stirred for 30 min at rt. It was then acidified with 1 M aq. HCl (2 mL) and extracted with IPA/CHCl3 (1:2, 50 mL). The organic layer was separated, dried over Na2SO4, and concentrated in vacuo to yield 4-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-3-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]-4-oxo-butanoic acid (0.029 g, 100%).

Workup

  1. extractionextracted with IPA/CHCl3 (1:2, 50 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0acadcd56f234ea887c866d1bc9c482c
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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