1-Methyl-3-aminopyrazole → 4-(3-Chloro-4-cyano-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

HRID 1177174Notes

Reaction equation

HRID 1177174 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][N:4]([CH3:7])[N:3]=1.C[O:9][C:10]([C:12]1[CH:22]=[C:21]([O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[C:26]([Cl:32])[CH:25]=2)[C:15]2[CH2:16][C:17]([CH3:20])([CH3:19])[O:18][C:14]=2[CH:13]=1)=O>>[CH3:7][N:4]1[CH:5]=[CH:6][C:2]([NH:1][C:10]([C:12]2[CH:22]=[C:21]([O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[C:26]([Cl:32])[CH:25]=3)[C:15]3[CH2:16][C:17]([CH3:20])([CH3:19])[O:18][C:14]=3[CH:13]=2)=[O:9])=[N:3]1

Participants

3

Reactant 2

HCID 1372541-Methyl-3-aminopyrazoleHCID 667558564-(3-Chloro-4-cyano-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

Product 1

HCID 667555724-(3-Chloro-4-cyano-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

Procedure

The title compound was prepared in a similar manner as described for Example 1, from 3-amino-1-methyl-pyrazole (157 mg, 1.62 mmol) and 4-(3-chloro-4-cyano-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (189a) (58 mg, 0.16 mmol) to give a white solid (53 mg, 77% yield). 1H NMR (400 MHz, CDCl3) δ 8.55 (s, 1 H) 7.91 (d, J=8.34 Hz, 2 H) 7.07 (dd, J=16.67, 8.34 Hz, 4 H) 6.78 (s, 1 H) 3.78 (s, 3 H) 2.90 (s, 2 H) 1.50 (s, 6 H); LCMS for C22H19ClN4O3 m/z 423.00 (M+H+).

Sources & evidence

ORD record
ord-eca95b690ea64074a163997d113f025e
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

Loading…