2-(Aminomethyl)thiazole-4-carbonitrile → HCID 57519832, compound

HRID 83130Notes

Reaction equation

HRID 83130 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=1.[NH2:24][CH2:25][C:26]1[S:27][CH:28]=[C:29]([C:31]#[N:32])[N:30]=1>>[C:31]([C:29]1[N:30]=[C:26]([CH2:25][NH:24][C:19](=[O:21])[C:18]2[CH:22]=[CH:23][C:15]([O:14][CH2:13][C:3]3[C:4]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)=[N:5][O:6][C:2]=3[CH3:1])=[N:16][CH:17]=2)[S:27][CH:28]=1)#[N:32]

Participants

3

Reactant 2

HCID 101540912-(Aminomethyl)thiazole-4-carbonitrileHCID 665992136-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid

Product 1

HCID 57519832HCID 57519832, compoundYield 68%

Procedure

As described for example 18, 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid (200 mg, 0.64 mmol) was converted using 2-aminomethyl-thiazole-4-carbonitrile instead of aminomethyl-isoxazolidin-3-one to the title compound (SiO2, heptane:ethyl acetate=90:10 to 40:60, 188 mg, 68%) which was obtained as a white solid. MS: m/e=432.3 [M−H]+.

Sources & evidence

ORD record
ord-e61da18d1a8a42e5b7bf5a43ea6babe0
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Reaction notes

Loading…