3-cyclopentyl-2-[6-oxo-4-(2-pyrrolidin-1-yl-phenoxy)-6H-pyridazin-1-yl]propionic acid → HCID 44463245, compound
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[N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:13]=[N:12]2)[C:8](O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:30][C:31]1[CH:35]=[CH:34][N:33]([CH2:36][C:37]([CH3:40])([OH:39])[CH3:38])[N:32]=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[N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:13]=[N:12]2)[C:8]([NH:30][C:31]2[CH:35]=[CH:34][N:33]([CH2:36][C:37]([OH:39])([CH3:38])[CH3:40])[N:32]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1Participants
Procedure
Using the method described in Example 17, 3-cyclopentyl-2-[6-oxo-4-(2-pyrrolidin-1-yl-phenoxy)-6H-pyridazin-1-yl]-propionic acid (Intermediate 51) and 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (Intermediate 1) afforded 3-cyclopentyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-2-[6-oxo-4-(2-pyrrolidin-1-yl-phenoxy)-6H-pyridazin-1-yl]-propionamide as a yellow solid (0.50 g, 34%); ES+-HRMS m/e calcd for C29H38N6O4 [M+H+] 535.3028 found 535.3027. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.05 (s, 3H), 1.06 (s, 3H), 1.08 (m, 1H), 1.25-1.73 (m, 8H), 1.83 (m, 4H), 1.93 (m, 1H), 2.25 (m, 1H), 3.22 (m, 4H), 3.89 (s, 2H), 4.67 (s, 1H), 5.44 (dd, J=4.5, J=10.7 Hz, 1H), 5.54 (d, J=2.9 Hz, 1H), 6.39 (d, J=2.3 Hz, 1H), 6.79 (m, 1H), 6.89 (dd, Jo=8.3 Hz, Jm=1.1 Hz, 1H), 7.09 (dd, Jo=7.9 Hz, Jm=1.5 Hz, 1H), 7.19 (m, 1H), 7.52 (d, J=2.3 Hz, 1H), 8.12 (d, J=2.9 Hz, 1H), 10.80 (s, 1H).
Sources & evidence
- ORD record
- ord-18856e87db6f4f39b697554efb988e0a
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258134B2
Reaction notes
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