Hydrochloric Acid → 3-(2,6-Dichlorophenyl)-5-methylisoxazole-4-carboxylic acid (4-dimethylamino-4-phenylcyclohexyl)amide hydrochloride

HRID 418315Notes

Reaction equation

HRID 418315 reaction equation
[Cl:1]C1C=CC=C(Cl)C=1C1C(C(O)=O)=C(C)ON=1.Cl.[CH3:19][N:20]([CH3:50])[C:21]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:26][CH2:25][CH:24]([NH:27][C:28]([C:30]2[C:31]([C:36]3[C:41]([Cl:42])=[CH:40][CH:39]=[CH:38][C:37]=3[Cl:43])=[N:32][O:33][C:34]=2[CH3:35])=[O:29])[CH2:23][CH2:22]1.Cl[Si](C)(C)C.C(OC(C)C)(C)C>CC(=O)CC.O.C(OCC)(=O)C.CO.C(OCC)C.CO.C(OCC)C>[ClH:1].[CH3:50][N:20]([CH3:19])[C:21]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:26][CH2:25][CH:24]([NH:27][C:28]([C:30]2[C:31]([C:36]3[C:41]([Cl:42])=[CH:40][CH:39]=[CH:38][C:37]=3[Cl:43])=[N:32][O:33][C:34]=2[CH3:35])=[O:29])[CH2:23][CH2:22]1

Participants

12

Reactant 5

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 7914Diisopropyl EtherHCID 775214-Isoxazolecarboxylic acid, 3-(2,6-dichlorophenyl)-5-methyl-HCID 666514093-(2,6-Dichlorophenyl)-5-methylisoxazole-4-carboxylic acid (4-dimethylamino-4-phenylcyclohexyl)amide

Product 1

HCID 666517533-(2,6-Dichlorophenyl)-5-methylisoxazole-4-carboxylic acid (4-dimethylamino-4-phenylcyclohexyl)amide hydrochloride

Reagents, catalysts & solvents 6

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolventHCID 21864698Diethyl ether methanolSolvent2×

Procedure

As described for Example 120, 650 mg of a cis-trans mixture of N,N-dimethyl-1-phenlcyclohexane-1,4-diamine were reacted with 810 mg 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylic acid (1 molar equivalent) and the crude product (1.92 g) was isolated. The main fraction, obtained after column chromatography on silica gel (3.0×19 cm) with 175 ml diethyl ether followed by 250 ml diethyl ether/methanol (V:V=2:1), 250 ml diethyl ether/methanol (V:V=1:1) and 100 ml methanol, of 1.10 g was dissolved in 15 ml 2-butanone and 15 ml ethyl acetate and converted into the corresponding hydrochloride of the non-polar diastereoisomer of 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylic acid (4-dimethylamino-4-phenylcyclohexyl)amide by adding 42 μl water, 296 μl chlorotrimethylsilane and 25 ml diisopropylether (311 mg of white solid).

Workup

  1. customthe crude product (1.92 g) was isolated

Sources & evidence

ORD record
ord-b1fea5c7c76749088190dfec620caf31
Source dataset
uspto-grants-2012_01
Patent number
US08093272B2

Reaction notes

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