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

HRID 2381420Notes

Reaction equation

HRID 2381420 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.[Cl:29][C:30]1[N:34]([CH3:35])[N:33]=[C:32]([NH2:36])[CH:31]=1>>[Cl:29][C:30]1[N:34]([CH3:35])[N:33]=[C:32]([NH:36][C:8](=[O:9])[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:26])[F:28])[CH:13]=[N:12]2)[CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:31]=1

Participants

3

Reactant 2

HCID 212799995-Chloro-1-methyl-1H-pyrazol-3-amine2×HCID 579191393-cyclopentyl-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionic acid2×

Product 1

HCID 44462996N-(5-chloro-1-methyl-1H-pyrazol-3-yl)-3-cyclopentyl-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionamideYield 30.6%

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 5-chloro-1-methyl-1H-pyrazol-3-ylamine (Intermediate 6) afforded N-(5-chloro-1-methyl-1H-pyrazol-3-yl)-3-cyclopentyl-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionamide as a white solid (51.7 mg, 30.6%); ES+-HRMS m/e calcd for C23H23N5O3F3Cl [M+H+] 510.1515 found 510.1514. 1H-NMR (300 MHz, DMSO-d6) δ ppm 0.98-1.84 (m, 9H), 1.93 (m, 1H), 2.23 (m, 1H), 3.70 (s, 3H), 5.44 (dd, J=4.4, J=10.4 Hz, 1H), 5.92 (d, J=3.0 Hz, 1H), 6.48 (s, 1H), 7.49-7.64 (m, 2H), 7.83 (t, J=7.9 Hz, 1H), 7.90 (d, J=7.9 Hz, 1H), 8.18 (d, J=3.0 Hz, 1H), 10.95 (s, 1H).

Sources & evidence

ORD record
ord-deb98038e77347edb748a0c34fcf6ba8
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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