3-Amino-5-bromo-1-methyl-1,2-dihydropyridin-2-one → N-(3-(5-Amino-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-methylphenyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxamide

HRID 1363515Notes

Reaction equation

HRID 1363515 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15]([C:17]3[S:21][C:20]4[CH2:22][CH2:23][CH2:24][CH2:25][C:19]=4[CH:18]=3)=[O:16])[C:9]=2[CH3:26])[N:5]=[C:4]([O-])[C:3]1=[O:28].[Na+].N[C:31]1C(=O)N(C)C=C(Br)C=1>>[NH2:5][C:4]1[C:3](=[O:28])[N:2]([CH3:1])[CH:7]=[C:6]([C:8]2[C:9]([CH3:26])=[C:10]([NH:14][C:15]([C:17]3[S:21][C:20]4[CH2:22][CH2:23][CH2:24][CH2:25][C:19]=4[CH:18]=3)=[O:16])[CH:11]=[CH:12][CH:13]=2)[CH:31]=1

Participants

3

Reactant 2

HCID 529112683-Amino-5-bromo-1-methyl-1,2-dihydropyridin-2-oneHCID 57625105Sodium 4-methyl-6-(2-methyl-3-(4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxamido)phenyl)-3-oxo-3,4-dihydropyrazin-2-olate

Product 1

HCID 57625113N-(3-(5-Amino-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-methylphenyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxamideYield 28%

Procedure

Using the same general procedure as described for the preparation of 10, 42 (3.67 g) gave a 28% yield (2.10 g) of 43 as a yellow solid: mp 210-211° C.; 1H NMR (500 MHz, DMSO-d6) δ 9.78 (bs, 1H), 7.65 (s, 1H), 7.25 (dd, 1H, J=1.5, 8.0 Hz), 7.21 (t, 1H, J=7.5 Hz), 7.09 (dd, 1H, J=1.0, 7.0 Hz), 6.89 (d, 1H, J=2.0 Hz), 6.43 (d, 1H, J=2.5 Hz), 5.19 (bs, 2H), 3.49 (s, 3H), 2.75 (m, 2H), 2.62 (m, 2H), 2.12 (s, 3H), 1.77 (m, 4H); MS (ESI+) m/z 394 (M+H).

Sources & evidence

ORD record
ord-5b0635bac2434c1ba756b474b04f7708
Source dataset
uspto-grants-2011_02
Patent number
US07884108B2

Reaction notes

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