1-Methyl-3-aminopyrazole → 5-[2,2-Dimethyl-6-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2,3-dihydro-benzofuran-4-yloxy]-pyridine-2-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

HRID 1177137Notes

Reaction equation

HRID 1177137 reaction equation
[C:1]([C:4]1[CH:14]=[C:13]([O:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]([OH:24])=O)=[N:20][CH:21]=2)[C:7]2[CH2:8][C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[CH:5]=1)(O)=[O:2].[NH2:25][C:26]1[CH:30]=[CH:29][N:28]([CH3:31])[N:27]=1>>[CH3:31][N:28]1[CH:29]=[CH:30][C:26]([NH:25][C:22]([C:19]2[CH:18]=[CH:17][C:16]([O:15][C:13]3[C:7]4[CH2:8][C:9]([CH3:12])([CH3:11])[O:10][C:6]=4[CH:5]=[C:4]([C:1](=[O:2])[NH:25][C:26]4[CH:30]=[CH:29][N:28]([CH3:31])[N:27]=4)[CH:14]=3)=[CH:21][N:20]=2)=[O:24])=[N:27]1

Participants

3

Reactant 2

HCID 1372541-Methyl-3-aminopyrazoleHCID 595601385-(6-Carboxy-2,2-dimethyl-2,3-dihydro-benzofuran-4-yloxy)-pyridine-2-carboxylic acid

Product 1

HCID 595601875-[2,2-Dimethyl-6-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2,3-dihydro-benzofuran-4-yloxy]-pyridine-2-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

Procedure

The title compound was prepared in a similar manner as described for Example 149, from 5-(6-carboxy-2,2-dimethyl-2,3-dihydro-benzofuran-4-yloxy)-pyridine-2-carboxylic acid (163b) (111 mg, 0.288 mmol) and 3-amino-1-methyl-pyrazole (56 mg, 0.576 mmol) to give a white solid (112 mg, 80% yield). 1H NMR (400 MHz, CDCl3) δ 10.19 (s, 1 H) 8.98 (s, 1 H) 8.30 (d, J=2.53 Hz, 1 H) 8.22 (d, J=8.59 Hz, 1 H) 7.28-7.38 (m, 2 H) 7.24-7.28 (m, 1 H) 7.07 (d, J=3.03 Hz, 2 H) 6.79 (d, J=2.02 Hz, 1 H) 6.83 (d, J=2.27 Hz, 1 H) 3.84 (s, 3 H) 3.74 (s, 3 H) 2.89 (s, 2 H) 1.49 (s, 6 H); LCMS for C25H25N7O4 m/z 488.20 (M+H+); Anal. Calcd. for C25H25N7O4.0.1 CHCl3: C, 59.50; H, 5.15; N, 19.35. Found: C, 59.77; H, 5.17; N, 18.96.

Sources & evidence

ORD record
ord-3b54eafd66e147ce8fe3d296fd3892a2
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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