3-cyclopentyl-2-(4-cyclopentylmethoxy-6-oxo-6H-pyridazin-1-yl)-propionic acid → 3-cyclopentyl-2-(4-cyclopentylmethoxy-6-oxo-6H-pyridazin-1-yl)-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamide
Reaction equation
[CH:1]1([CH2:6][CH:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][CH2:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:13]=[N:12]2)[C:8](O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:25][C:26]1[CH:30]=[CH:29][N:28]([CH2:31][C:32]([CH3:35])([OH:34])[CH3:33])[N:27]=1>>[CH:1]1([CH2:6][CH:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][CH2:19][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24]3)[CH:13]=[N:12]2)[C:8]([NH:25][C:26]2[CH:30]=[CH:29][N:28]([CH2:31][C:32]([OH:34])([CH3:33])[CH3:35])[N:27]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1Participants
Reactant 2
Product 1
Procedure
Using the method described in Example 1, 3-cyclopentyl-2-(4-cyclopentylmethoxy-6-oxo-6H-pyridazin-1-yl)-propionic acid (Intermediate 59) and 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (Intermediate 1) afforded 3-cyclopentyl-2-(4-cyclopentylmethoxy-6-oxo-6H-pyridazin-1-yl)-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamide as a white solid (22.2 mg, 10%); ES+-HRMS m/e calcd for C25H37N5O4 [M+H+] 472.2919, found 472.2922. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.05 (s, 3H), 1.06 (s, 3H), 1.05 (m, 1H), 1.25-1.97 (m, 18H), 2.26 (m, 1H), 3.89 (s, 2H), 3.90 (d, J=5.8 Hz, 2H), 4.67 (s, 1H), 5.46 (dd, J=4.2, J=11.2 Hz, 1H), 6.27 (d, J=2.8 Hz, 1H), 6.39 (d, J=2.2 Hz, 1H), 7.52 (d, J=2.2 Hz, 1H), 7.82 (d, J=2.8 Hz, 1H), 10.73 (s, 1H).
Sources & evidence
- ORD record
- ord-9787ac18843943c7ae9fa89a3bda9482
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258134B2
Reaction notes
Loading…