Phenethylamine → N-(4-Methyl-5-phenethylcarbamoylthiazol-2-yl)isonicotinamide

HRID 45322Notes

Reaction equation

HRID 45322 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:10][C:11]1[N:12]=[C:13]([NH:19][C:20]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[O:21])[S:14][C:15]=1[C:16](O)=[O:17]>>[CH3:10][C:11]1[N:12]=[C:13]([NH:19][C:20](=[O:21])[C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[S:14][C:15]=1[C:16](=[O:17])[NH:9][CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 1001PhenethylamineHCID 822263324-Methyl-2-[(pyridine-4-carbonyl)amino]thiazole-5-carboxylic acid

Product 1

HCID 59369643N-(4-Methyl-5-phenethylcarbamoylthiazol-2-yl)isonicotinamideYield 34%

Procedure

Following the procedure as described in Example 1, making variations only as required to use phenethylamine in place of benzylamine to react with 4-methyl-2-[(pyridine-4-carbonyl)amino]thiazole-5-carboxylic acid, the title compound was obtained as a white solid in 34% yield; 1H NMR (DMSO-d6, 300 MHz) δ 13.2 (s, br, 1H), 8.89-8.66 (m, 2H), 8.16-7.88 (m, 3H), 7.29-7.14 (m, 5H), 3.47-3.32 (m, 2H), 2.81-2.65 (m, 2H), 2.46 (s, 3H); MS (ES+) m/z 367.2 (M+1).

Sources & evidence

ORD record
ord-cbf11126a2814b7384c6273ba356d233
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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