Hydrochloric Acid → 6-((5-Isobutyl-1-phenyl-1H-pyrazole-3-yl)methylcarbamoyl)-3-azabicyclo[3.1.0]hexane hydrochloride

HRID 340747Notes

Reaction equation

HRID 340747 reaction equation
[ClH:1].[CH2:2]([C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:9]=[C:8]([CH2:17][NH:18][C:19]([CH:21]2[CH:26]3[CH:22]2[CH2:23][N:24](C(OC(C)(C)C)=O)[CH2:25]3)=[O:20])[CH:7]=1)[CH:3]([CH3:5])[CH3:4].CCCCCC.C(OCC)(=O)C>CO>[ClH:1].[CH2:2]([C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:9]=[C:8]([CH2:17][NH:18][C:19]([CH:21]2[CH:26]3[CH:22]2[CH2:23][NH:24][CH2:25]3)=[O:20])[CH:7]=1)[CH:3]([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 8857Ethyl AcetateHCID 117700883tert-Butyl 6((5-isobutyl-1-phenyl-1H-pyrazole-3-yl)methylcarbamoyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate

Product 1

HCID 1177004486-((5-Isobutyl-1-phenyl-1H-pyrazole-3-yl)methylcarbamoyl)-3-azabicyclo[3.1.0]hexane hydrochlorideYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.25 M hydrochloric acid solution (9.76 mL, 12.2 mmol) dissolved in methanol was added dropwise to the tert-butyl 6-((5-isobutyl-1-phenyl-1H-pyrazole-3-yl)methylcarbamoyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate (268 mg, 0.610 mmol) prepared in Example 10 and stirred for 3 hours. The completion of the reaction was confirmed by TLC (hexane:ethyl acetate=1:2). After the reaction was completed, the reaction mixture was concentrated under reduced pressure to obtain 229 mg (100%) of the target compound.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8d02873c20dc487c96c2ce1f58a328a2
Source dataset
uspto-grants-2014_11
Patent number
US08895602B1

Reaction notes

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