1-Methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid → N-(3-fluoro-4-(2-(4-(methylcarbamoyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide

HRID 1676332Notes

Reaction equation

HRID 1676332 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]4[CH:25]=[CH:24][C:19]([C:20]([NH:22][CH3:23])=[O:21])=[CH:18][CH:17]=4)[S:15][C:8]=23)=[C:4]([F:28])[CH:3]=1.[CH3:29][N:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36](O)=[O:37])[C:31]1=[O:39]>>[F:28][C:4]1[CH:3]=[C:2]([NH:1][C:36]([C:32]2[C:31](=[O:39])[N:30]([CH3:29])[CH:35]=[CH:34][CH:33]=2)=[O:37])[CH:27]=[CH:26][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[CH:13]=[C:14]([C:16]3[CH:25]=[CH:24][C:19]([C:20](=[O:21])[NH:22][CH3:23])=[CH:18][CH:17]=3)[S:15][C:8]=12

Participants

3

Reactant 2

HCID 12015101-Methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acidHCID 673486984-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-N-methylbenzamide

Product 1

HCID 58949464N-(3-fluoro-4-(2-(4-(methylcarbamoyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxamideYield 30%

Procedure

Prepared from 4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-N-methylbenzamide (Example 95, Step A) and 1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid according to the procedure of Example 89. The crude was purified by silica gel flash column chromatography (3% MeOH in CH2Cl2) to afford 11.1 mg (30%) of the desired product. LRMS (ESI pos) m/e 529.2 (M+1). 1H NMR (400 MHz, CDCl3/CD3OD) δ 8.59 (dd, 1H), 8.46 (d, 1H), 8.01 (dd, 1H), 7.94 (m, 2H), 7.88 (m, 3H), 7.67 (s, 1H), 7.47 (m, 1H), 7.36 (t, 1H), 6.64 (m, 2H), 3.75 (s, 3H), 2.98 (s, 3H); 19F NMR (376 MHz, CDCl3/CD3OD) 6-128.2.

Workup

  1. customThe crude was purified by silica gel flash column chromatography (3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-bf6d24f20580407085accd474efac278
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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