1-Methyl-3-aminopyrazole → 4-[4-(Azetidine-1-carbonyl)-phenoxy]-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

HRID 1643569Notes

Reaction equation

HRID 1643569 reaction equation
[N:1]1([C:5]([C:7]2[CH:27]=[CH:26][C:10]([O:11][C:12]3[C:17]4[CH2:18][C:19]([CH3:22])([CH3:21])[O:20][C:16]=4[CH:15]=[C:14]([C:23](O)=[O:24])[CH:13]=3)=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.[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:23]([C:14]2[CH:13]=[C:12]([O:11][C:10]3[CH:9]=[CH:8][C:7]([C:5]([N:1]4[CH2:2][CH2:3][CH2:4]4)=[O:6])=[CH:27][CH:26]=3)[C:17]3[CH2:18][C:19]([CH3:21])([CH3:22])[O:20][C:16]=3[CH:15]=2)=[O:24])=[N:30]1

Participants

3

Reactant 2

HCID 1372541-Methyl-3-aminopyrazoleHCID 595598464-[4-(Azetidine-1-carbonyl)-phenoxy]-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid

Product 1

HCID 247680204-[4-(Azetidine-1-carbonyl)-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 15, from 4-[4-(azetidine-1-carbonyl)-phenoxy]-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (35c) (598 mg, 1.63 mmol) and 1-methyl-3-aminopyrazole (236 mg, 2.43 mmol) to give a white solid (315 mg, 41% yield). 1H NMR (400 MHz, CDCl3) δ 8.31 (s, 1 H) 7.65 (ddd, J=9.22, 2.78, 2.40 Hz, 2 H) 7.28 (d, J=2.27 Hz, 1 H) 7.02 (dd, J=9.85, 1.26 Hz, 2 H) 6.98 (ddd, J=9.22, 2.78, 2.40 Hz, 2 H) 6.78 (d, J=2.02 Hz, 1 H) 4.30-4.40 (m, 2 H) 4.19-4.30 (m, 2 H) 3.81 (s, 3 H) 2.89 (s, 2 H) 2.32-2.40 (m, 2 H) 1.49 (s, 6 H); LCMS for C25H26N4O4 m/z 447.20 (M+H)+; Anal. Calcd. for C25H26N4O4.0.31 H2O: C, 65.38; H, 6.02; N, 12.20; Found: C, 65.37; H, 5.85; N, 12.38.

Sources & evidence

ORD record
ord-77fb678b67034c6cbcb04e1c680e8a15
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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