1-Methyl-3-aminopyrazole → 3-cyclopentyl-N-(1-methyl-1H-pyrazol-3-yl)-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionamide

HRID 2381421Notes

Reaction equation

HRID 2381421 reaction equation
[CH:1]1([CH2:6][CH:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:28])([F:27])[F:26])[CH:13]=[N:12]2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:29][N:30]1[CH:34]=[CH:33][C:32]([NH2:35])=[N:31]1>>[CH:1]1([CH2:6][CH:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:28])([F:27])[F:26])[CH:13]=[N:12]2)[C:8]([NH:35][C:32]2[CH:33]=[CH:34][N:30]([CH3:29])[N:31]=2)=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 1372541-Methyl-3-aminopyrazoleHCID 579191393-cyclopentyl-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionic acid2×

Product 1

HCID 444637743-cyclopentyl-N-(1-methyl-1H-pyrazol-3-yl)-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionamideYield 65%

Procedure

Using the method described in Example 11, 3-cyclopentyl-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionic acid (Intermediate 21) and 1-methyl-1H-pyrazol-3-ylamine afforded 3-cyclopentyl-N-(1-methyl-1H-pyrazol-3-yl)-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionamide as a white solid (78.7 mg, 65%); ES+-HRMS m/e calcd for C23H24N5O3F3 [M+H+] 476.1904 found 476.1902. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.06 (m, 1H), 1.26-1.77 (m, 8H), 1.91 (m, 1H), 2.25 (m, 1H), 3.73 (s, 3H), 5.46 (dd, J=4.6, J=10.5 Hz, 1H), 5.92 (d, J=3.0 Hz, 1H), 6.36 (d, J=2.1 Hz, 1H), 7.54 (d, J=2.1 Hz, 1H), 7.56-7.60 (m, 2H), 7.83 (t, J=7.8 Hz, 1H), 7.90 (d, J=7.8 Hz, 1H), 8.17 (d, J=3.0 Hz, 1H), 10.75 (s, 1H).

Sources & evidence

ORD record
ord-13aeb77b1b5641f5a5b951faa2c2e5ae
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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