2-methyl-2H-1,2,3-triazol-4-amine hydrochloride → 4-(4-Cyano-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (2-methyl-2H-[1,2,3]triazol-4-yl)-amide

HRID 1643645Notes

Reaction equation

HRID 1643645 reaction equation
Cl.[CH3:2][N:3]1[N:7]=[C:6]([NH2:8])[CH:5]=[N:4]1.C[O:10][C:11]([C:13]1[CH:23]=[C:22]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][CH:26]=2)[C:16]2[CH2:17][C:18]([CH3:21])([CH3:20])[O:19][C:15]=2[CH:14]=1)=O>>[CH3:2][N:3]1[N:7]=[C:6]([NH:8][C:11]([C:13]2[CH:23]=[C:22]([O:24][C:25]3[CH:26]=[CH:27][C:28]([C:31]#[N:32])=[CH:29][CH:30]=3)[C:16]3[CH2:17][C:18]([CH3:21])([CH3:20])[O:19][C:15]=3[CH:14]=2)=[O:10])[CH:5]=[N:4]1

Participants

3

Reactant 2

HCID 509986482-methyl-2H-1,2,3-triazol-4-amine hydrochlorideHCID 667558044-(4-Cyano-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

Product 1

HCID 667557244-(4-Cyano-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (2-methyl-2H-[1,2,3]triazol-4-yl)-amide

Procedure

The title compound was prepared in a similar manner as described for Example 1, from 2-methyl-2H-1,2,3-triazol-4-amine hydrochloride (533 mg, 1.78 mmol) and 4-(4-cyano-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (187a) (128 mg, 0.396 mmol) to give a white solid (130 mg, 84% yield). 1H NMR (400 MHz, CDCl3) δ 8.82 (s, 1 H) 8.07 (s, 1 H) 7.62 (d, J=8.59 Hz, 2 H) 7.09 (d, J=10.36 Hz, 2 H) 7.02 (d, J=8.59 Hz, 2 H) 4.07 (s, 3 H) 2.88 (s, 2 H) 1.49 (s, 6 H); LCMS for C21H19N5O3 m/z 390.20 (M+H+).

Sources & evidence

ORD record
ord-52b0f89e536c4cfdbcce897931ba82e7
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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