3-cyclopentyl-2-[4-(2-methanesulfonyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid → HCID 57919327, compound

HRID 2381437Notes

Reaction equation

HRID 2381437 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[S:25]([CH3:28])(=[O:27])=[O:26])[CH:13]=[N:12]2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]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>>[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[S:25]([CH3:28])(=[O:27])=[O:26])[CH:13]=[N:12]2)[C:8]([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:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 579191503-cyclopentyl-2-[4-(2-methanesulfonyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 57919327HCID 57919327, compoundYield 54%

Procedure

Using the method described in Example 17, 3-cyclopentyl-2-[4-(2-methanesulfonyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (Intermediate 48) 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-[4-(2-methanesulfonyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionamide as a white solid (0.74 g, 54%); ES+-HRMS m/e calcd for C26H33N5O6S [M+Na+] 566.2044 found 566.2045. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.05 (s, 3H), 1.06 (s, 3H), 1.10 (m, 1H), 1.28-1.76 (m, 8H), 1.92 (m, 1H), 2.28 (m, 1H), 3.36 (s, 3H), 3.89 (s, 2H), 4.67 (s, 1H), 5.48 (dd, J=4.4, J=10.9 Hz, 1H), 5.96 (d, J=2.8 Hz, 1H), 6.41 (d, J=2.2 Hz, 1H), 7.53 (d, J=2.2 Hz, 1H), 7.56-7.66 (m, 2H), 7.87 (m, 1H), 8.00 (dd, Jo=8.0 Hz, Jm=1.6 Hz, 1H), 8.21 (d, J=2.8 Hz, 1H), 10.83 (s, 1H).

Sources & evidence

ORD record
ord-f260b479d5cc48c5bc069fc4d9df7fac
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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