1-Methyl-5-(trifluoromethyl)-1H-pyrazol-3-amine → 3-cyclopentyl-N-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionamide

HRID 2381451Notes

Reaction equation

HRID 2381451 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](O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:29][N:30]1[C:34]([C:35]([F:38])([F:37])[F:36])=[CH:33][C:32]([NH2:39])=[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:27])([F:28])[F:26])[CH:13]=[N:12]2)[C:8]([NH:39][C:32]2[CH:33]=[C:34]([C:35]([F:36])([F:37])[F:38])[N:30]([CH3:29])[N:31]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 229127981-Methyl-5-(trifluoromethyl)-1H-pyrazol-3-amine2×HCID 579191393-cyclopentyl-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionic acid2×

Product 1

HCID 579192953-cyclopentyl-N-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionamideYield 10%

Procedure

Using the method described in Example 17, 3-cyclopentyl-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionic acid (Intermediate 21) and 1-methyl-5-trifluoromethyl-1H-pyrazol-3-ylamine (Intermediate 9) afforded 3-cyclopentyl-N-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionamide as a yellow solid (35.3 mg, 10%); ES+-HRMS m/e calcd for C24H23N5O3F6 [M+Na+] 566.1597 found 566.1596. 1H-NMR (400 MHz, CDCl3) δ ppm 1.08-1.24 (m, 2H), 1.44-1.84 (m, 7H), 2.24 (t, J=7.5 Hz, 2H), 3.85 (s, 3H), 5.56 (t, J=7.5 Hz, 1H), 5.98 (d, J=3.0 Hz, 1H), 7.06 (s, 1H), 7.21 (d, J=7.9 Hz, 1H), 7.44 (t, J=7.9 Hz, 1H), 7.65 (t, J=7.9 Hz, 1H), 7.77 (d, J=7.9 Hz, 1H), 7.94 (d, J=3.0 Hz, 1H), 8.79 (s, 1H).

Sources & evidence

ORD record
ord-bd58ec0cdda24acda8e122d1f56ee5c9
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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