1-Methyl-3-aminopyrazole → 4-Isopropoxy-2-phenoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

HRID 1177207Notes

Reaction equation

HRID 1177207 reaction equation
C(O[C:6]([C:8]1[CH:24]=[C:23]([O:25][CH:26]([CH3:28])[CH3:27])[C:11]2[CH2:12][CH:13]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:14][C:10]=2[CH:9]=1)=[O:7])(C)(C)C.[CH3:29][N:30]1[CH:34]=[CH:33][C:32]([NH2:35])=[N:31]1>O>[CH3:29][N:30]1[CH:34]=[CH:33][C:32]([NH:35][C:6]([C:8]2[CH:24]=[C:23]([O:25][CH:26]([CH3:28])[CH3:27])[C:11]3[CH2:12][CH:13]([CH2:15][O:16][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[O:14][C:10]=3[CH:9]=2)=[O:7])=[N:31]1

Participants

4

Reactant 2

HCID 1372541-Methyl-3-aminopyrazoleHCID 59560151HCID 59560151, compound

Product 1

HCID 595602044-Isopropoxy-2-phenoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared in a similar manner as described for Example 200 from 4-isopropoxy-2-phenoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester (214c) and 1-methyl-3-aminopyrazole. 1H NMR (400 MHz, CDCl3) δ 8.69 (s, 1 H) 7.28-7.32 (m, 3 H) 7.05 (s, 1 H) 6.93-7.00 (m, 3 H) 6.89 (s, 1 H) 6.84 (s, 1 H) 5.19-5.27 (m, 1 H) 4.64-4.72 (m, 1 H) 4.20-4.26 (m, 1 H) 4.11 (dd, J=9.98, 4.67 Hz, 1 H) 3.82 (s, 3 H) 3.35 (dd, J=16.42, 9.35 Hz, 1 H) 3.11 (dd, J=16.55, 6.95 Hz, 1 H) 1.36 (d, J=5.81 Hz, 6 H); LCMS for C23H25N3O4 m/z 408.20 (M+H)+; Anal. Calcd. for C23H25N3O4.0.50 H2O: C, 66.33; H, 6.29; N, 10.09. Found: C, 66.29; H, 6.05; N, 9.87.

Sources & evidence

ORD record
ord-ce58e9ff87764c58b7b433a017ee8bd6
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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