1-(Cyclopropylmethyl)piperidin-4-amine → 5-[5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl]thiophene-2-sulfonic acid (1-cyclopropylmethylpiperidin-4-yl)amide hydrochloride

HRID 1921421Notes

Reaction equation

HRID 1921421 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].[CH:20]1([CH2:23][N:24]2[CH2:29][CH2:28][CH:27]([NH2:30])[CH2:26][CH2:25]2)[CH2:22][CH2:21]1>>[ClH:19].[CH:20]1([CH2:23][N:24]2[CH2:29][CH2:28][CH:27]([NH:30][S:16]([C:14]3[S:15][C:11]([C:5]4[CH:4]=[C:3]([CH2:1][CH3:2])[C:8](=[O:9])[NH:7][C:6]=4[CH3:10])=[CH:12][CH:13]=3)(=[O:18])=[O:17])[CH2:26][CH2:25]2)[CH2:21][CH2:22]1

Participants

3

Reactant 2

HCID 172216241-(Cyclopropylmethyl)piperidin-4-amineHCID 866103525-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonyl chloride

Product 1

HCID 116985145-[5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl]thiophene-2-sulfonic acid (1-cyclopropylmethylpiperidin-4-yl)amide hydrochlorideYield 58%

Procedure

5-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-sulfonyl chloride is reacted with (1-cyclopropylmethylpiperidin-4-yl)amine as described in Steps 5 and 6, Example 24 to give the title compound as a white solid (58% yield). LC/MS: RT 2.07 min; m/e 436; 1H NMR (δ, ppm): 11.85 (1H, br), 10.18 (1H, br), 8.30 (1H, d), 7.57 (1H, d), 7.34 (1H, s), 7.17 (1H, d), 3.30-3.58 (2H, m), 2.80-3.08 (2H, m), 2.40 (2H, q), 2.33 (3H, s), 1.72-2.18 (4H, m), 1.00-1.20 (4H, m), 0.60 (2H, m), 0.35 (2H, m).

Sources & evidence

ORD record
ord-0d5db943693a44ad8e5a26660b879428
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

Loading…