5-(aminomethyl)-N,N-dimethylpyridin-2-amine → 5-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonic acid [(6-dimethylaminopyridin-3-yl)methyl]amide hydrochloride

HRID 1921423Notes

Reaction equation

HRID 1921423 reaction equation
[CH2:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:10])=[C:5]([C:11]2[S:15][C:14]([S:16]([Cl:19])(=[O:18])=[O:17])=[CH:13][CH:12]=2)[CH:4]=1)[CH3:2].[CH3:20][N:21]([CH3:30])[C:22]1[N:27]=[CH:26][C:25]([CH2:28][NH2:29])=[CH:24][CH:23]=1>>[ClH:19].[CH3:20][N:21]([CH3:30])[C:22]1[N:27]=[CH:26][C:25]([CH2:28][NH:29][S:16]([C:14]2[S:15][C:11]([C:5]3[CH:4]=[C:3]([CH2:1][CH3:2])[C:8](=[O:9])[NH:7][C:6]=3[CH3:10])=[CH:12][CH:13]=2)(=[O:18])=[O:17])=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 167885965-(aminomethyl)-N,N-dimethylpyridin-2-amineHCID 866103525-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonyl chloride

Product 1

HCID 116341615-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonic acid [(6-dimethylaminopyridin-3-yl)methyl]amide hydrochlorideYield 55%

Procedure

5-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonyl chloride is reacted with [(6-dimethylaminopyridin-3-yl)methyl]amine as described in Steps 5 and 6, Example 24 to give the title compound as a yellow solid (55% yield). LC/MS: RT 2.07 min; m/e 433; 1H NMR (δ, ppm): 11.86 (1H, br), 8.57 (1H, t), 7.80-7.95 (2H, m), 7.54 (1H, d), 7.43 (1H, s), 7.21 (1H, d), 7.14 (1H, d), 4.03 (2H, d), 3.17 (6H, d), 2.41 (2H, q), 2.30 (3H, s), 1.10 (3H, t).

Sources & evidence

ORD record
ord-341b157d60874f6baf73271d27514cd3
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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