HCID 57919178, compound → HCID 57919107, compound

HRID 2381445Notes

Reaction equation

HRID 2381445 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:28]=[CH:27][CH:26]=[C:25]4[C:20]=3[CH:21]=[CH:22][CH:23]=[N:24]4)[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:28]=[CH:27][CH:26]=[C:25]4[C:20]=3[CH:21]=[CH:22][CH:23]=[N:24]4)[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])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 57919178HCID 57919178, compound2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 57919107HCID 57919107, compoundYield 59%

Procedure

Using the method described in Example 17, 3-cyclopentyl-2-[6-oxo-4-(quinolin-5-yloxy)-6H-pyridazin-1-yl]-propionic acid (Intermediate 57) 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-(quinolin-5-yloxy)-6H-pyridazin-1-yl]-propionamide as a white solid (0.69 g, 59%); ES+-HRMS m/e calcd for C28H32N6O4 [M+H+] 517.2558 found 517.2557. 1H-NMR (300 MHz, DMSO-d6) δ ppm 1.04 (s, 3H), 1.05 (s, 3H), 1.10 (m, 1H), 1.21-1.77 (m, 8H), 1.92 (m, 1H), 2.28 (m, 1H), 3.89 (s, 2H), 4.67 (s, 1H), 5.46 (dd, J=4.4, J=10.7 Hz, 1H), 5.78 (d, J=2.7 Hz, 1H), 6.40 (d, J=2.1 Hz, 1H), 7.52 (d, J=2.1 Hz, 1H), 7.57 (d, Jo=7.8 Hz, 1H), 7.62 (dd, Jo=8.5, 4.0 Hz, 1H), 7.86 (t, Jo=8.2 Hz, 1H), 8.04 (d, Jo=8.5 Hz, 1H), 8.29 (d, J=2.7 Hz, 1H), 8.39 (d, Jo=8.5 Hz, 1H), 9.01 (dd, Jo=4.0, Jm=1.5 Hz, 1H), 10.81 (s, 1H).

Sources & evidence

ORD record
ord-d84c2096e1944499a3436db2dd6ac932
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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