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

HRID 1643675Notes

Reaction equation

HRID 1643675 reaction equation
C(O[C:6]([C:8]1[CH:19]=[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11]2[CH2:12][CH:13]([CH2:15][O:16][CH3:17])[O:14][C:10]=2[CH:9]=1)=[O:7])(C)(C)C.[CH3:28][N:29]1[CH:33]=[CH:32][C:31]([NH2:34])=[N:30]1>>[CH3:28][N:29]1[CH:33]=[CH:32][C:31]([NH:34][C:6]([C:8]2[CH:19]=[C:18]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:11]3[CH2:12][CH:13]([CH2:15][O:16][CH3:17])[O:14][C:10]=3[CH:9]=2)=[O:7])=[N:30]1

Participants

3

Reactant 2

HCID 1372541-Methyl-3-aminopyrazoleHCID 595600924-Benzyloxy-2-methoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester

Product 1

HCID 595600244-Benzyloxy-2-methoxymethyl-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 200, from 4-benzyloxy-2-methoxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester (204b) and 1-methyl-3-aminopyrazole (268 mg, 2.95 mmol) to give a white solid (645 mg, 83% yield). 1H NMR (400 MHz, CDCl3) δ 8.53 (s, 1 H) 7.34-7.44 (m, 5 H) 7.29 (d, J=2.27 Hz, 1 H) 7.09 (d, J=1.26 Hz, 1 H) 6.89 (s, 1 H) 6.82 (d, J=2.27 Hz, 1 H) 5.12 (s, 2 H) 5.01-5.09 (m, 1 H) 3.79 (s, 3 H) 3.56-3.66 (m, 2 H) 3.45 (s, 3 H) 3.29 (dd, J=16.42, 9.60 Hz, 1 H) 3.01 (dd, J=16.42, 7.33 Hz, 1 H); LCMS for C22H23N3O4 m/z 394.00 (M+H)+.

Sources & evidence

ORD record
ord-aabe6f19a48e4c5c985ec6fd731e698e
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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