HCID 57919214, compound → HCID 44463772, compound

HRID 2381541Notes

Reaction equation

HRID 2381541 reaction equation
[Cl:1][C:2]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[CH:6]=[N:7][N:8]([CH:12]([CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:13]([OH:15])=O)[C:9](=[O:11])[CH:10]=1.[NH2:29][C:30]1[CH:34]=[CH:33][N:32]([CH2:35][C:36]([CH3:39])([OH:38])[CH3:37])[N:31]=1>>[Cl:1][C:2]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:3]=1[O:4][C:5]1[CH:6]=[N:7][N:8]([CH:12]([CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:13]([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:15])[C:9](=[O:11])[CH:10]=1

Participants

3

Reactant 2

HCID 57919214HCID 57919214, compound2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 44463772HCID 44463772, compoundYield 63%

Procedure

Using the method described in Example 49, 2-[4-(2-chloro-4-methoxy-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclohexyl-propionic acid (Intermediate 90) and 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (Intermediate 1) afforded 2-[4-(2-chloro-4-methoxy-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclohexyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamide as an off-white solid (190 mg, 63%); ES+-HRMS m/e calcd for C27H34N5O5Cl [M+H+] 544.2321 found 544.2324. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.88-1.22 (m, 6H), 1.05 (s, 3H), 1.06 (s, 3H), 1.62 (br. s., 5H), 1.74-1.88 (m, 1H), 2.06-2.24 (m, 1H), 3.81 (s, 3H), 3.89 (s, 2H), 4.67 (s, 1H), 5.53 (dd, J=11.2, 3.9 Hz, 1H), 5.65 (d, J=2.7 Hz, 1H), 6.39 (d, J=1.8 Hz, 1H), 7.04 (dd, J=9.0, 3.0 Hz, 1H), 7.27 (d, J=3.0 Hz, 1H), 7.43 (d, J=9.0 Hz, 1H), 7.52 (d, J=1.8 Hz, 1H), 8.18 (d, J=2.7 Hz, 1H), 10.83 (s, 1H).

Sources & evidence

ORD record
ord-f3c8fcfcbe79475dac6547ebf547c36d
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

Loading…