3-Phenylpropylamine → N-[4-Methyl-5-(3-phenylpropylcarbamoyl)thiazol-2-yl]isonicotinamide

HRID 45323

Reaction equation

HRID 45323 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][C:12]1[N:13]=[C:14]([NH:20][C:21]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=[O:22])[S:15][C:16]=1[C:17](O)=[O:18]>>[CH3:11][C:12]1[N:13]=[C:14]([NH:20][C:21](=[O:22])[C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[S:15][C:16]=1[C:17](=[O:18])[NH:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 162593-PhenylpropylamineHCID 822263324-Methyl-2-[(pyridine-4-carbonyl)amino]thiazole-5-carboxylic acid

Product 1

HCID 59369685N-[4-Methyl-5-(3-phenylpropylcarbamoyl)thiazol-2-yl]isonicotinamideYield 22%

Procedure

Following the procedure as described in Example 1, making variations only as required to use 3-phenylpropylamine 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 22% yield; 1H NMR (DMSO-d6, 300 MHz) δ 8.78-8.76 (m, 2H), 8.13-7.93 (m, 3H), 7.27-7.11 (m, 5H), 3.32-3.11 (m, 2H), 2.70-2.46 (m, 5H), 1.84-1.72 (m, 2H); MS (ES+) m/z 381.1 (M+1).

Sources & evidence

ORD record
ord-76ba2f13db9f462a8148fc192cfdc1c6
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Linked notes

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