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

HRID 418313Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 418313
FC1C=C(C2(N(C)C)CCC(N)CC2)C=CC=1.[Cl:18]C1C=CC=C(Cl)C=1C1C(C(O)=O)=C(C)ON=1.Cl.[CH3:36][N:37]([CH3:68])[C:38]1([C:61]2[CH:66]=[CH:65][CH:64]=[C:63]([F:67])[CH:62]=2)[CH2:43][CH2:42][CH:41]([NH:44][C:45]([C:47]2[C:48]([C:53]3[C:58]([Cl:59])=[CH:57][CH:56]=[CH:55][C:54]=3[Cl:60])=[N:49][O:50][C:51]=2[CH3:52])=[O:46])[CH2:40][CH2:39]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:18].[CH3:68][N:37]([CH3:36])[C:38]1([C:61]2[CH:66]=[CH:65][CH:64]=[C:63]([F:67])[CH:62]=2)[CH2:43][CH2:42][CH:41]([NH:44][C:45]([C:47]2[C:48]([C:53]3[C:58]([Cl:59])=[CH:57][CH:56]=[CH:55][C:54]=3[Cl:60])=[N:49][O:50][C:51]=2[CH3:52])=[O:46])[CH2:40][CH2:39]1

Komponenten

13

Edukt 6

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 7914Diisopropyl EtherHCID 775214-Isoxazolecarboxylic acid, 3-(2,6-dichlorophenyl)-5-methyl-HCID 116916703-(2,6-Dichlorophenyl)-5-methylisoxazole-4-carboxylic acid [4-dimethylamino-4-(3-fluorophenyl)cyclohexyl]amideHCID 579041991-(3-fluorophenyl)-N,N-dimethylcyclohexane-1,4-diamine

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6569Methyl Ethyl KetoneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 21864698Diethyl ether methanolLösungsmittel2×

Versuchsvorschrift

As described for Example 120, 700 mg of a cis-trans mixture of 1-(3-fluorophenyl)-N,N-dimethylcyclohexane-1,4-diamine were reacted with 810 mg 3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxylic acid (1 molar equivalent) and the crude product (1.86 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 950 mg was dissolved in 25 ml 2-butanone and 25 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-(3-fluorophenyl)cyclohexyl]amide by adding 35 μl water, 246 μl chlorotrimethylsilane and 25 ml diisopropylether (263 mg of white solid, Mp. 248-250° C.).

Aufarbeitung

  1. customthe crude product (1.86 g) was isolated

Quellen und Nachweise

ORD-Eintrag
ord-2bd0baf0b472493a8e8581b51adcf54d
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093272B2

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