2-[4-(2-tert-butyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid → HCID 44465054, compound

HRID 2381511Notes

Reaction equation

HRID 2381511 reaction equation
[C:1]([C:5]1[CH:28]=[CH:27][CH:26]=[CH:25][C:6]=1[O:7][C:8]1[CH:9]=[N:10][N:11]([CH:15]([CH2:19][CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[C:16]([OH:18])=O)[C:12](=[O:14])[CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:29][C:30]1[CH:34]=[CH:33][N:32]([CH2:35][C:36]([CH3:39])([OH:38])[CH3:37])[N:31]=1>>[C:1]([C:5]1[CH:28]=[CH:27][CH:26]=[CH:25][C:6]=1[O:7][C:8]1[CH:9]=[N:10][N:11]([CH:15]([CH2:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24]2)[C:16]([NH:29][C:30]2[CH:34]=[CH:33][N:32]([CH2:35][C:36]([OH:38])([CH3:37])[CH3:39])[N:31]=2)=[O:18])[C:12](=[O:14])[CH:13]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 579192262-[4-(2-tert-butyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 44465054HCID 44465054, compound

Procedure

Using the method described in Example 49, 2-[4-(2-tert-butyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid (Intermediate 68) and 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (Intermediate 1) afforded 2-[4-(2-tert-butyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamide was obtained as an off-white solid (1.05 g, 77%); ES+-HRMS m/e calcd for C29H39N5O4 [M+H+] 522.3075 found 522.3077. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.03-1.08 (m, 8H), 1.32 (s, 9H), 1.37-1.78 (m, 7H), 1.81-2.02 (m, 1H), 2.17-2.36 (m, 1H), 3.89 (s, 2H), 4.67 (s, 1H), 5.47 (dd, J=10.7, 4.3 Hz, 1H), 5.79 (d, J=2.8 Hz, 1H), 6.40 (d, J=2.1 Hz, 1H), 7.16 (d, J=7.9 Hz, 1H), 7.23-7.30 (m, 1H), 7.31-7.38 (m, 1H), 7.50 (dd, J=7.8, 1.4 Hz, 1H), 7.53 (d, J=2.1 Hz, 1H), 8.15 (d, J=2.8 Hz, 1H), 10.81 (s, 1H).

Sources & evidence

ORD record
ord-b2498e8702804560ac195a7733ad38d8
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

Loading…