2-Chlorobenzylamine → 5-{5-[(2-Chlorobenzylamino)methyl]thiophen-2-yl}-3-ethyl-6-methyl-1H-pyridin-2-one hydrochloride

HRID 1921473Notes

Reaction equation

HRID 1921473 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]([CH:16]=O)=[CH:13][CH:12]=2)[CH:4]=1)[CH3:2].[Cl:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][NH2:22]>>[ClH:18].[Cl:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][NH:22][CH2:16][C:14]1[S:15][C:11]([C:5]2[CH:4]=[C:3]([CH2:1][CH3:2])[C:8](=[O:9])[NH:7][C:6]=2[CH3:10])=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 666482-ChlorobenzylamineHCID 588085435-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-carbaldehyde

Product 1

HCID 674922995-{5-[(2-Chlorobenzylamino)methyl]thiophen-2-yl}-3-ethyl-6-methyl-1H-pyridin-2-one hydrochlorideYield 98%

Procedure

5-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-carbaldehyde is reacted with 2-chlorobenzylamine as described in Method A, Example 123 to give the title compound as a yellow solid (98% yield). LC/MS: RT 2.22 min; m/e 373 (M+H); 1H NMR (CD3OD, δ, ppm): 7.70 (2H, m), 7.0-7.58 (7H, m), 4.53 (2H, s), 4.28-4.47 (4H, d), 3.55 (1H, m), 2.62 (2H, q), 2.46 (3H, s), 4.46 (4H, d), 1.20 (3H, t).

Sources & evidence

ORD record
ord-92f726f4514349d4a1390c5449f4b7f3
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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