6-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester → 6-[(3-Butyl-5-methyl-isoxazol-4-ylmethyl)-amino]-N-isopropyl-nicotinamide

HRID 1807545Notes

Reaction equation

HRID 1807545 reaction equation
CO[C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([NH: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.COC(=O)C1C=CC(OC[C:34]2[C:35]([CH2:40]CCC)=[N:36]OC=2C)=NC=1>>[CH2:18]([C:13]1[C:12]([CH2:11][NH:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([NH:36][CH:35]([CH3:40])[CH3:34])=[O:22])=[CH:5][N:6]=2)=[C:16]([CH3:17])[O:15][N:14]=1)[CH2:19][CH2:20][CH3:21]

Participants

3

Reactant 2

HCID 665991586-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl esterHCID 66643788Methyl 6-(((3-butyl-5-methylisoxazol-4-yl)methyl)amino)nicotinate

Product 1

HCID 498016106-[(3-Butyl-5-methyl-isoxazol-4-ylmethyl)-amino]-N-isopropyl-nicotinamideYield 70%

Procedure

As described for example 5d, 6-[(3-butyl-5-methyl-isoxazol-4-ylmethyl)-amino]-nicotinic acid methyl ester (90 mg, 0.3 mmol) was converted, instead of 6-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester, to the title compound (69 mg, 70%) which was obtained as a white foam after purification by chromatography (silica, 0 to 7% methanol in dichloromethane). MS: m/e=331.4 [M+H]+.

Sources & evidence

ORD record
ord-a8b6b7458bc84d2b886562c740a67b7e
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

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