Cyclopropylamine → 6-((3-Butyl-5-methyl-isoxazol-4-yl)methoxy)-N-cyclopropyl-nicotinamide

HRID 1807495Notes

Reaction equation

CO[C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1.[CH:23]1([NH2:26])[CH2:25][CH2:24]1>>[CH2:18]([C:13]1[C:12]([CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([NH:26][CH:23]3[CH2:25][CH2:24]3)=[O:22])=[CH:5][N:6]=2)=[C:16]([CH3:17])[O:15][N:14]=1)[CH2:19][CH2:20][CH3:21]

Participants

Reactant 2

HCID 69828Cyclopropylamine

HCID 665991586-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester

Product 1

HCID 498047576-((3-Butyl-5-methyl-isoxazol-4-yl)methoxy)-N-cyclopropyl-nicotinamideYield 17%

Procedure

As described for example 5d, 6-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (537 mg, 1.5 mmol) was converted, using cyclopropylamine instead of isopropylamine, to the title compound (85 mg, 17%) which was obtained as a white solid after purification by chromatography (silica, 0 to 50% ethyl acetate in heptane). MS: m/e=330.4 [M+H]+.

Sources & evidence

ORD record: ord-22c3fc458a3e4e34bc41f428f2804c8d
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357703B2

Reaction notes

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