1-Methyl-3-aminopyrazole → 4-(4-(Dimethylcarbamoyl)-3-fluorophenoxy)-2-methyl-N-(1-methyl-1H-pyrazol-3-yl)benzofuran-6-carboxamide

HRID 1643731Notes

Reaction equation

HRID 1643731 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[C:9]([CH3:11])[O:10][C:6]=2[CH:5]=[C:4]([C:12]([O:14]CC)=O)[CH:3]=1.[F:17][C:18]1[CH:28]=[C:27](F)[CH:26]=[CH:25][C:19]=1[C:20]([N:22]([CH3:24])[CH3:23])=[O:21].[CH3:30][N:31]1[CH:35]=[CH:34][C:33]([NH2:36])=[N:32]1>>[CH3:23][N:22]([CH3:24])[C:20]([C:19]1[CH:25]=[CH:26][C:27]([O:1][C:2]2[C:7]3[CH:8]=[C:9]([CH3:11])[O:10][C:6]=3[CH:5]=[C:4]([C:12]([NH:36][C:33]3[CH:34]=[CH:35][N:31]([CH3:30])[N:32]=3)=[O:14])[CH:3]=2)=[CH:28][C:18]=1[F:17])=[O:21]

Participants

4

Reactant 3

HCID 1372541-Methyl-3-aminopyrazoleHCID 11514065Ethyl 4-hydroxy-2-methylbenzofuran-6-carboxylateHCID 606372302,4-difluoro-N,N-dimethylbenzamide

Product 1

HCID 595601684-(4-(Dimethylcarbamoyl)-3-fluorophenoxy)-2-methyl-N-(1-methyl-1H-pyrazol-3-yl)benzofuran-6-carboxamide

Procedure

The title compound was prepared in a similar manner as described for Example 271, from ethyl 4-hydroxy-2-methylbenzofuran-6-carboxylate (0.275 g, 1.25 mmol), 2,4-difluoro-N,N-dimethylbenzamide (0.289 g, 1.56 mmol) and 1-methyl-1H-pyrazol-3-amine (0.21 g, 2.12 mmol) in two steps to give a solid (5 mg, 1% yield) as expected product. 1H NMR (400 MHz, DMSO-d6) δ 10.90 (s, 1 H) 8.12 (s, 1H) 7.61-7.62 (m, 2 H) 7.38-7.42 (t, 1 H) 7.03-7.06 (m, 1 H) 6.88-6.91 (m, 1 H) 6.58-6.59 (m, 1 H) 6.50 (m, 1H) 3.78 (s, 3 H) 3.00 (s, 3 H) 2.88 (m, 3 H) 2.47-2.48 (m, 3 H). LCMS for C23H21FN4O4 m/z 437.20 (M+H)+.

Workup

  1. customThe title compound was prepared in a similar manner

Sources & evidence

ORD record
ord-f51d0610d3554cf29029d1a93d1b21fd
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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