Cyclopropylamine → N-Cyclopropyl-6-(3-phenyl-5-trifluoromethyl-isoxazol-4-ylmethoxy)-nicotinamide

HRID 1897155Notes

Reaction equation

HRID 1897155 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:14][O:15][C:16]=2[C:17]([F:20])([F:19])[F:18])=[N:6][CH:5]=1.COC(=O)C1C=CC(OCC2C(C3C=CC(Cl)=CC=3)=NOC=2C)=NC=1.[CH:53]1([NH2:56])[CH2:55][CH2:54]1>>[CH:53]1([NH:56][C:3](=[O:2])[C:4]2[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]3[C:13]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)=[N:14][O:15][C:16]=3[C:17]([F:19])([F:18])[F:20])=[N:6][CH:5]=2)[CH2:55][CH2:54]1

Participants

4

Reactant 3

HCID 69828CyclopropylamineHCID 426293306-[3-(4-Chloro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl esterHCID 684432696-(3-Phenyl-5-trifluoromethyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester

Product 1

HCID 68941876N-Cyclopropyl-6-(3-phenyl-5-trifluoromethyl-isoxazol-4-ylmethoxy)-nicotinamideYield 94%

Procedure

As described for example 89, 6-(3-phenyl-5-trifluoromethyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (100 mg, 0.26 mmol), instead of 6-[3-(4-chloro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester, was converted, using cylopropylamine instead of morpholine, to the title compound (100 mg, 94%) which was obtained as a white solid. MS: m/e=404.5 [M+H]+.

Sources & evidence

ORD record
ord-ce76868b11664f0dae97989c12fce193
Source dataset
uspto-grants-2013_08
Patent number
US08518974B2

Reaction notes

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