HCID 57919185, compound → 3-cyclopentyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-2-[6-oxo-4-(2-piperidin-1-yl-phenoxy)-6H-pyridazin-1-yl]-propionamide

HRID 2381434Notes

Reaction equation

HRID 2381434 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[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:13]=[N:12]2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:31][C:32]1[CH:36]=[CH:35][N:34]([CH2:37][C:38]([CH3:41])([OH:40])[CH3:39])[N:33]=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[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:13]=[N:12]2)[C:8]([NH:31][C:32]2[CH:36]=[CH:35][N:34]([CH2:37][C:38]([OH:40])([CH3:39])[CH3:41])[N:33]=2)=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 57919185HCID 57919185, compound2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 579191573-cyclopentyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-2-[6-oxo-4-(2-piperidin-1-yl-phenoxy)-6H-pyridazin-1-yl]-propionamideYield 55%

Procedure

Using the method described in Example 17, 3-cyclopentyl-2-[6-oxo-4-(2-piperidin-1-yl-phenoxy)-6H-pyridazin-1-yl]-propionic acid (Intermediate 52) 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-piperidin-1-yl-phenoxy)-6H-pyridazin-1-yl]-propionamide as a white solid (0.79 g, 55%); ES+-HRMS m/e calcd for C30H40N6O4 [M+H+] 549.3184 found 549.3186. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.05 (s, 3H), 1.06 (s, 3H), 1.08 (m, 1H), 1.32 (m, 1H), 1.40 (br.s., 8H), 1.49-1.71 (m, 5H), 1.93 (m, 1H), 2.31 (m, 1H), 2.89 (m, 4H), 3.89 (s, 2H), 4.67 (s, 1H), 5.52 (dd, J=3.9, J=11.4 Hz, 1H), 5.71 (d, J=2.8 Hz, 1H), 6.39 (d, J=2.3 Hz, 1H), 7.09 (m, 1H), 7.13 (dd, Jo=8.1 Hz, Jm=1.3 Hz, 1H), 7.21 (dd, Jo=7.9 Hz, Jm=1.5 Hz, 1H), 7.28 (m, 1H), 7.52 (d, J=2.3 Hz, 1H), 8.01 (d, J=2.8 Hz, 1H), 10.73 (s, 1H).

Sources & evidence

ORD record
ord-ba6a343a28bd41e7a39859b618c7498e
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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