Hydrochloric Acid → 4-((4-chlorophenyl)((3,7-dimethylbenzo[d]isoxazol-5-yl)amino)methyl)-1-(2,4-dimethoxypyrimidin-5-yl)-5-isopropyl-1H-pyrazole-3-carboxylic acid

HRID 873889Notes

Reaction equation

HRID 873889 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:32][C:33]2[CH:34]=[C:35]([CH3:43])[C:36]3[O:40][N:39]=[C:38]([CH3:41])[C:37]=3[CH:42]=2)[C:9]2[C:10]([C:27]([O:29]CC)=[O:28])=[N:11][N:12]([C:17]3[C:18]([O:25][CH3:26])=[N:19][C:20]([O:23][CH3:24])=[N:21][CH:22]=3)[C:13]=2[CH:14]([CH3:16])[CH3:15])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([NH:32][C:33]2[CH:34]=[C:35]([CH3:43])[C:36]3[O:40][N:39]=[C:38]([CH3:41])[C:37]=3[CH:42]=2)[C:9]2[C:10]([C:27]([OH:29])=[O:28])=[N:11][N:12]([C:17]3[C:18]([O:25][CH3:26])=[N:19][C:20]([O:23][CH3:24])=[N:21][CH:22]=3)[C:13]=2[CH:14]([CH3:15])[CH3:16])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 117702629ethyl 4-((4-chlorophenyl)((3,7-dimethylbenzo[d]isoxazol-5-yl)amino)-methyl)-1-(2,4-dimethoxypyrimidin-5-yl)-5-isopropyl-1H-pyrazole-3-carboxylate

Product 1

HCID 1177028274-((4-chlorophenyl)((3,7-dimethylbenzo[d]isoxazol-5-yl)amino)methyl)-1-(2,4-dimethoxypyrimidin-5-yl)-5-isopropyl-1H-pyrazole-3-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of ethyl 4-((4-chlorophenyl)((3,7-dimethylbenzo[d]isoxazol-5-yl)amino)-methyl)-1-(2,4-dimethoxypyrimidin-5-yl)-5-isopropyl-1H-pyrazole-3-carboxylate (Step 46.12) (455 mg, 0.677 mmol) in MeOH (10 mL) cooled down to 0° C. was added dropwise 4M NaOH (2.54 mL, 10.15 mmol). The reaction mixture was allowed to warm up and stir at RT for 45 min, acidified with 4N HCl and MeOH was removed under reduced pressure. The aq. layer was extracted with EtOAc, combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford the title product (450 mg, 0.663 mmol, 98% yield) as a beige amorphous solid. tR: 1.20 min (LC-MS 2); ESI-MS: 577 [M+H]+, ESI-MS: 575 [M−H]− (LC-MS 2).

Workup

  1. temperatureto warm up
  2. customwas removed under reduced pressure
  3. extractionThe aq. layer was extracted with EtOAc
  4. washwere washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-26bd9b6f6365479ab70a848ab67e7a4f
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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