Nicotinoyl chloride → HCID 59369674, compound

HRID 45351Notes

Reaction equation

[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH2:10]([NH:17][C:18]([C:20]1[S:24][C:23]([NH2:25])=[N:22][C:21]=1[CH3:26])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([NH:17][C:18]([C:20]1[S:24][C:23]([NH:25][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=2)=[N:22][C:21]=1[CH3:26])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Reactant 2

HCID 82604Nicotinoyl chloride

HCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

Product 1

HCID 59369674HCID 59369674, compoundYield 33%

Procedure

Following the procedure as described in Example 2, making variations only as required to use nicotinoyl chloride in place of benzoyl chloride to react with 2-amino-4-methylthiazole-5-carboxylic acid benzylamide, the title compound was obtained as a white solid in 33% yield. m.p. 224-226° C.; 1H NMR (DMSO-d6, 300 MHz) δ 9.17 (d, J=1.5 Hz, 1H), 8.76 (dd, J=1.5, 4.6 Hz, 1H), 8.63 (t, J=5.7 Hz, 1H), 8.40-8.36 (m, 1H), 7.55 (dd, J=4.6, 8.1 Hz, 1H), 7.33-7.19 (m, 5H), 4.38 (d, J=5.7 Hz, 2H), 2.51 (s, 3H); MS (ES+) m/z 353.2 (M+1).

Sources & evidence

ORD record: ord-d373f29b07a74de9ba7061d7aec38635
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541457B2

Reaction notes

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