HCID 57919098, compound → HCID 44464799, compound

HRID 2381446Notes

Reaction equation

HRID 2381446 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:20]=[CH:21][CH:22]=[C:23]4[C:28]=3[N:27]=[CH:26][CH:25]=[CH:24]4)[CH:13]=[N:12]2)[C:8](O)=[O:9])[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:20]=[CH:21][CH:22]=[C:23]4[C:28]=3[N:27]=[CH:26][CH:25]=[CH: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:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 57919098HCID 57919098, compound2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 44464799HCID 44464799, compoundYield 25%

Procedure

Using the method described in Example 17, 3-cyclopentyl-2-[6-oxo-4-(quinolin-8-yloxy)-6H-pyridazin-1-yl]-propionic acid (Intermediate 55) 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-8-yloxy)-6H-pyridazin-1-yl]-propionamide as an off-white solid (0.34 g, 25%); ES+-HRMS m/e calcd for C28H32N6O4 [M+H+] 517.2558 found 517.2558. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.04 (s, 3H), 1.06 (s, 3H), 1.10 (m, 1H), 1.27-1.76 (m, 8H), 1.91 (m, 1H), 2.23 (m, 1H), 3.89 (s, 2H), 4.67 (s, 1H), 5.44 (dd, J=4.5, J=10.9 Hz, 1H), 5.50 (d, J=2.9 Hz, 1H), 6.40 (d, J=2.2 Hz, 1H), 7.52 (d, J=2.2 Hz, 1H), 7.65 (dd, Jo=8.3, 4.2 Hz, 1H), 7.72 (t, Jo=7.9 Hz, 1H), 7.76 (dd, Jo=7.5 Hz, Jm=1.5 Hz, 1H), 8.03 (dd, Jo=8.1 Hz, Jm=1.5 Hz, 1H), 8.24 (d, J=2.9 Hz, 1H), 8.52 (dd, Jo=8.3 Hz, Jm=1.7 Hz, 1H), 8.92 (dd, Jo=4.2 Hz, Jm=1.7 Hz, 1H), 10.81 (s, 1H).

Sources & evidence

ORD record
ord-837258791caa4d61a2f3d6dcc5b55736
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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