Hydrochloric Acid → (S)-2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-(4-fluorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetic acid

HRID 472863Notes

Reaction equation

HRID 472863 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:12]([CH3:34])=[N:13][C:14]2[N:15]([N:24]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=3)[CH:26]=2)[C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([O:5][C@@H:6]([C:11]1[C:12]([CH3:34])=[N:13][C:14]2[N:15]([N:24]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=3)[CH:26]=2)[C:16]=1[C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66693648(S)-methyl 2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-(4-fluorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

Product 1

HCID 66693058(S)-2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-(4-fluorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetic acidYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (S)-methyl 2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-(4-fluorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (0.0475 g, 0.099 mmol) and 1M NaOH (0.986 ml, 0.986 mmol) in MeOH was heated at reflux for 3 h. Then, cooled, neutralized with 1M HCl (1 mL), concentrated and the residue was taken up in Et2O (25 mL), washed with water (5 mL), brine (5 mL), dried (MgSO4), filtered and concentrated to give (S)-2-(tert-butoxy)-2-(2-(3-chlorophenyl)-7-(4-fluorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetic acid (0.0407 g, 0.086 mmol, 87% yield) as while solid. 1H NMR (500 MHz, 13) δ: 7.87-7.83 (m, 2H), 7.82-7.78 (m, 1H), 7.75-7.71 (m, 1H), 7.36-7.28 (m, 4H), 6.90 (s, 1H), 5.19 (s, 1H), 2.67 (s, 3H), 1.02 (s, 9H). LCMS (M+H) calcd for C25H24ClFN3O3: 468.15. found: 468.2.

Workup

  1. temperatureat reflux for 3 h
  2. temperatureThen, cooled
  3. concentrationconcentrated
  4. washwashed with water (5 mL), brine (5 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0424c17fc12545ad887487710634b798
Source dataset
uspto-grants-2014_01
Patent number
US08633200B2

Reaction notes

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