Hydrochloric Acid → 3-(2,6-Dichlorophenyl)-5-methylisoxazole-4-carboxylic acid [4-di-methylamino-4-(3-fluorophenyl)cyclohexyl]amide hydrochloride

HRID 418314Notes

Reaction equation

HRID 418314 reaction equation
[CH3:1][N:2]([CH3:33])[C:3]1([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)[CH2:8][CH2:7][CH:6]([NH:9][C:10]([C:12]2[C:13]([C:18]3[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:25])=[N:14][O:15][C:16]=2[CH3:17])=[O:11])[CH2:5][CH2:4]1.C(OCC)(=O)C.Cl.Cl[Si](C)(C)C>CC(=O)CC.O.CO>[ClH:24].[CH3:33][N:2]([CH3:1])[C:3]1([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)[CH2:8][CH2:7][CH:6]([NH:9][C:10]([C:12]2[C:13]([C:18]3[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:25])=[N:14][O:15][C:16]=2[CH3:17])=[O:11])[CH2:5][CH2:4]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 8857Ethyl AcetateHCID 116916703-(2,6-Dichlorophenyl)-5-methylisoxazole-4-carboxylic acid [4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]amide

Product 1

HCID 666510833-(2,6-Dichlorophenyl)-5-methylisoxazole-4-carboxylic acid [4-di-methylamino-4-(3-fluorophenyl)cyclohexyl]amide hydrochloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

As described for Example 122, 448 mg of the polar diastereoisomer of 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylic-acid [4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]amide were obtained, which, dissolved in 15 ml 2-butanone, 15 ml ethyl acetate and 2 ml methanol, were converted into the corresponding hydrochloride by adding 16.5 μl water, 116 μl chlorotrimethylsilane and 25 ml diusopropylether (364 mg of white solid, Mp. 246-248° C.).

Workup

  1. customwere obtained

Sources & evidence

ORD record
ord-ca3e899430664d5c897c6481e22a9c1a
Source dataset
uspto-grants-2012_01
Patent number
US08093272B2

Reaction notes

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