2-Amino-5-methylpyridine → 4-(4-(Dimethylcarbamoyl)-3-fluorophenoxy)-N-(5-methylpyridin-2-yl)benzofuran-6-carboxamide

HRID 1643784Notes

Reaction equation

HRID 1643784 reaction equation
C(O[C:4]([C:6]1[CH:14]=[C:13]([OH:15])[C:9]2[CH:10]=[CH:11][O:12][C:8]=2[CH:7]=1)=[O:5])C.[F:16][C:17]1[CH:27]=[C:26](F)[CH:25]=[CH:24][C:18]=1[C:19]([N:21]([CH3:23])[CH3:22])=[O:20].[NH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][N:31]=1>>[CH3:22][N:21]([CH3:23])[C:19]([C:18]1[CH:24]=[CH:25][C:26]([O:15][C:13]2[C:9]3[CH:10]=[CH:11][O:12][C:8]=3[CH:7]=[C:6]([C:4]([NH:29][C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][N:31]=3)=[O:5])[CH:14]=2)=[CH:27][C:17]=1[F:16])=[O:20]

Participants

4

Reactant 3

HCID 153482-Amino-5-methylpyridineHCID 11344757Ethyl 4-hydroxybenzofuran-6-carboxylateHCID 606372302,4-difluoro-N,N-dimethylbenzamide

Product 1

HCID 595600084-(4-(Dimethylcarbamoyl)-3-fluorophenoxy)-N-(5-methylpyridin-2-yl)benzofuran-6-carboxamide

Procedure

The title compound was prepared in a similar manner as described for Example 341, from ethyl 4-hydroxy-benzofuran-6-carboxylate (8a) (0.26 g, 1.24 mmol), 2,4-difluoro-N,N-dimethylbenzamide (0.287 g, 1.55 mmol), and 2-amino-5-methyl pyridine (0.228 g, 2.11 mmol) (except that amide coupling was carried out at 75° C. for four hours) to give a solid (81 mg, 15% yield) as the expected product. 1H NMR (400 MHz, DMSO-d6) δ 10.84 (s, 1 H) 8.27 (s, 1 H) 8.22-8.23 (m, 1 H) 8.18-8.19 (m, 1 H)) 8.06-8.08 (d, 1 H) 7.67 (m, 1 H) 7.64 (m, 1 H) 7.39-7.44 (t, 1 H) 7.09-7.12 (m, 1 H) 6.95-6.97 (m, 1 H) 6.90 (m, 1 H) 3.00 (s, 3 H) 2.88 (m, 3 H) 2.28 (s, 3 H). LCMS for C24H20FN3O4 m/z 434.10 (M+H)+.

Workup

  1. customThe title compound was prepared in a similar manner

Sources & evidence

ORD record
ord-c67adf634c8e4db7ac61e083072337c2
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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