Sodium Hydroxide → 4-(((5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)amino)(4-chlorophenyl)methyl)-1-cyclopropyl-5-(trifluoromethyl)-1H-pyrazole-3-carboxylic acid

HRID 873866Notes

Reaction equation

HRID 873866 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[N:6]([CH3:9])[CH:5]=[C:4]([NH:10][CH:11]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[C:12]2[C:13]([C:24]([O:26]CC)=[O:25])=[N:14][N:15]([CH:21]3[CH2:23][CH2:22]3)[C:16]=2[C:17]([F:20])([F:19])[F:18])[CH:3]=1.[OH-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[C:7](=[O:8])[N:6]([CH3:9])[CH:5]=[C:4]([NH:10][CH:11]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[C:12]2[C:13]([C:24]([OH:26])=[O:25])=[N:14][N:15]([CH:21]3[CH2:23][CH2:22]3)[C:16]=2[C:17]([F:19])([F:18])[F:20])[CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 117702576ethyl 4-(((5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)amino)(4-chlorophenyl)-methyl)-1-cyclopropyl-5-(trifluoromethyl)-1H-pyrazole-3-carboxylate

Product 1

HCID 1177026994-(((5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)amino)(4-chlorophenyl)methyl)-1-cyclopropyl-5-(trifluoromethyl)-1H-pyrazole-3-carboxylic acidYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-(((5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)amino)(4-chlorophenyl)methyl)-1-cyclopropyl-5-(trifluoromethyl)-1H-pyrazole-3-carboxylate (Step 40.3) (350 mg, 0.569 mmol) in THF (3 mL) and MeOH (3 mL) was added 2M NaOH (2.84 mL, 5.69 mmol). The resulting mixture was stirred at RT for 1 hr. Volatiles were evaporated and the resulting aq. phase was adjusted to pH 5 with 2N HCl, extracted twice with EtOAc and the combined organic phases were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude was triturated in EtOAc to afford the title product (222 mg, 0.443 mmol, 78% yield) as an off-white solid. tR: 1.00 min (LC-MS 2); ESI-MS: 501/503 [M+H]+, ESI-MS: 499/501 [M−H]− (LC-MS 2).

Workup

  1. customVolatiles were evaporated
  2. extractionextracted twice with EtOAc
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was triturated in EtOAc

Sources & evidence

ORD record
ord-96a3dafce9fd48bdb094f1d53dd9ee3a
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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