1-Methylcyclopropanamine → 6-((3-Butyl-5-methyl-isoxazol-4-yl)methoxy)-N-(1-methyl-cyclopropyl)-nicotinamide

HRID 1807507Notes

Reaction equation

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

Participants

Reactant 2

HCID 116511491-Methylcyclopropanamine

HCID 665983356-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid

Product 1

HCID 498007356-((3-Butyl-5-methyl-isoxazol-4-yl)methoxy)-N-(1-methyl-cyclopropyl)-nicotinamideYield 70%

Procedure

As described for example 19b, 6-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid (100 mg, 0.34 mmol) was converted, using 1-methylcyclopropylamine instead of L-2,2,2-trifluoro-1-(methyl)ethylamine, to the title compound (83 mg, 70%) which was obtained as a white solid after purification by chromatography (silica, heptane:ethyl acetate=1:0 to 2:1). MS: m/e=342.3 [M−H]−.

Sources & evidence

ORD record: ord-dfc523bb78bf4571b34cc8c63013de3a
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357703B2

Reaction notes

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