Hydrochloric Acid → 4-[6-{[(1,1-dimethylethyl)oxy]carbonyl}-5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl]benzoic acid

HRID 1364118Notes

Reaction equation

HRID 1364118 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:18]=[C:17]3[C:11]([CH2:12][CH2:13][N:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:16]3)=[N:10]2)=[CH:5][CH:4]=1)#N.[OH-:26].[Na+].Cl.C(OCC)(=O)C.[OH2:35]>C(O)C>[CH3:24][C:22]([O:21][C:19]([N:14]1[CH2:15][CH2:16][C:17]2=[CH:18][N:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]([OH:35])=[O:26])=[CH:8][CH:7]=3)[N:10]=[C:11]2[CH2:12][CH2:13]1)=[O:20])([CH3:23])[CH3:25]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium Hydroxide2×HCID 669307651,1-Dimethylethyl 2-(4-cyanophenyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate

Product 1

HCID 669308134-[6-{[(1,1-dimethylethyl)oxy]carbonyl}-5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl]benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1,1-dimethylethyl 2-(4-cyanophenyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate (may be prepared as described in Description 10) (750 mg, 2.22 mmol) in ethanol (7.5 ml) was added 10% sodium hydroxide solution (7.5 ml), and the reaction heated at reflux, under argon, for 5 hours. 10% sodium hydroxide solution (10 ml) was added and stirring continued at reflux, under argon, overnight. The reaction was cooled to room temperature and the solvent partially reduced in vacuo. The resulting crude product was dissolved in water and acidified with 5N hydrochloric acid. Ethyl acetate was added, and the product extracted into ethyl acetate (×3). The combined organic fractions were dried over magnesium sulphate and solvent evaporated in vacuo to afford the title compound (D23). MS (ES−) m/e 356 [M−H]−.

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux, under argon, for 5 hours
  3. temperatureat reflux, under argon, overnight
  4. extractionthe product extracted into ethyl acetate (×3)
  5. dry with materialThe combined organic fractions were dried over magnesium sulphate and solvent
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-b104b464fbba4bfabbe7fcc6215f43e8
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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