methyl 3-amino-1-methyl-1H-pyrazole-5-carboxylate → 5-{3-cyclopentyl-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionylamino}-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester
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][O:30][C:31]([C:33]1[N:34]([CH3:39])[N:35]=[C:36]([NH2:38])[CH:37]=1)=[O:32]>>[CH3:29][O:30][C:31]([C:33]1[N:34]([CH3:39])[N:35]=[C:36]([NH:38][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:26])([F:27])[F:28])[CH:13]=[N:12]2)[CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:37]=1)=[O:32]Participants
Reactant 2
Product 1
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-amino-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (Intermediate 8) afforded 5-{3-cyclopentyl-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionylamino}-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester as a white solid (22.1 mg, 17%); ES+-HRMS m/e calcd for C25H26N5O5F3 [M+H+] 534.1959 found 534.1959. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.09 (m, 1H), 1.23-1.75 (m, 8H), 1.95 (m, 1H), 2.23 (m, 1H), 3.82 (s, 3H), 4.01 (s, 3H), 5.46 (dd, J=4.5, J=10.4 Hz, 1H), 5.93 (d, J=2.9 Hz, 1H), 6.95 (s, 1H), 7.53-7.60 (m, 2H), 7.83 (t, J=7.8 Hz, 1H), 7.90 (d, J=7.8 Hz, 1H), 8.19 (d, J=2.9 Hz, 1H), 11.06 (s, 1H).
Sources & evidence
- ORD record
- ord-a6064ed31fa04f679aa6b0c5705d82e4
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258134B2
Reaction notes
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