2-[4-(2-cyano-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid → 2-[4-(2-cyano-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamide
Reaction equation
[C:1]([C:3]1[CH:26]=[CH:25][CH:24]=[CH:23][C:4]=1[O:5][C:6]1[CH:7]=[N:8][N:9]([CH:13]([CH2:17][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[C:14](O)=[O:15])[C:10](=[O:12])[CH:11]=1)#[N:2].[NH2:27][C:28]1[CH:32]=[CH:31][N:30]([CH2:33][C:34]([CH3:37])([OH:36])[CH3:35])[N:29]=1>>[C:1]([C:3]1[CH:26]=[CH:25][CH:24]=[CH:23][C:4]=1[O:5][C:6]1[CH:7]=[N:8][N:9]([CH:13]([CH2:17][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[C:14]([NH:27][C:28]2[CH:32]=[CH:31][N:30]([CH2:33][C:34]([OH:36])([CH3:35])[CH3:37])[N:29]=2)=[O:15])[C:10](=[O:12])[CH:11]=1)#[N:2]Participants
Reactant 2
Product 1
Procedure
Using the method described in Example 17, 2-[4-(2-cyano-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid (Intermediate 58) and 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (Intermediate 1) afforded 2-[4-(2-cyano-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamide as a white solid (0.83 g, 58%); ES+-HRMS m/e calcd for C26H30N6O4 [M+H+] 491.2402 found 491.2402. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.05 (s, 3H), 1.06 (s, 3H), 1.08 (m, 1H), 1.28-1.76 (m, 8H), 1.94 (m, 1H), 2.29 (m, 1H), 3.89 (s, 2H), 4.67 (s, 1H), 5.49 (dd, J=4.3, J=10.9 Hz, 1H), 6.08 (d, J=2.8 Hz, 1H), 6.41 (d, J=2.3 Hz, 1H), 7.53 (d, J=2.3 Hz, 1H), 7.54 (td, Jo=7.7 Hz, Jm=0.9 Hz, 1H), 7.58 (d, Jo=8.1 Hz, 1H), 7.81-7.91 (m, 1H), 8.03 (dd, Jo=7.7 Hz, Jm=1.6 Hz, 1H), 8.24 (d, J=2.8 Hz, 1H), 10.83 (s, 1H).
Sources & evidence
- ORD record
- ord-b0984c57e1f6484fa13738fd1f5be02d
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258134B2
Reaction notes
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