Hydrochloric Acid → 5-Methyl-3-phenylisoxazole-4-carboxylic acid (4-dimethylamino-4-phenylcyclohexyl)amide hydrochloride

HRID 418318Notes

Reaction equation

HRID 418318 reaction equation
[CH3:1][N:2]([CH3:30])[C:3]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:8][CH2:7][CH:6]([NH:9][C:10]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])=[O:11])[CH2:5][CH2:4]1.Cl.[Cl:32][Si](C)(C)C.C(OC(C)C)(C)C>CC(=O)CC.C(OCC)(=O)C.O>[ClH:32].[CH3:30][N:2]([CH3:1])[C:3]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:8][CH2:7][CH:6]([NH:9][C:10]([C:12]2[C:13]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[N:14][O:15][C:16]=2[CH3:17])=[O:11])[CH2:5][CH2:4]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 7914Diisopropyl EtherHCID 666514015-Methyl-3-phenylisoxazole-4-carboxylic acid (4-dimethylamino-4-phenylcyclohexyl)amide

Product 1

HCID 666518365-Methyl-3-phenylisoxazole-4-carboxylic acid (4-dimethylamino-4-phenylcyclohexyl)amide hydrochloride

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

As described for Example 127, 190 mg of the polar diastereoisomer of 5-methyl-3-phenylisoxazole-4-carboxylic acid (4-dimethylamino-4-phenylcyclohexyl)amide were also obtained, which, dissolved in 10 ml 2-butanone and 5 ml ethyl acetate, were converted into the corresponding hydrochloride by adding 8.5 μl water, 60 μl chlorotrimethylsilane and 10 ml diisopropylether (135 mg of white solid, Mp. 243-245° C.).

Workup

  1. customwere also obtained

Sources & evidence

ORD record
ord-654de04990e9474394cdecfa96ab51cb
Source dataset
uspto-grants-2012_01
Patent number
US08093272B2

Reaction notes

Loading…