HCID 57919248, compound → HCID 57919202, compound

HRID 2381435Notes

Reaction equation

HRID 2381435 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]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:13]=[N:12]2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:25][C:26]1[CH:30]=[CH:29][N:28]([CH2:31][C:32]([CH3:35])([OH:34])[CH3:33])[N:27]=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]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:13]=[N:12]2)[C:8]([NH:25][C:26]2[CH:30]=[CH:29][N:28]([CH2:31][C:32]([OH:34])([CH3:33])[CH3:35])[N:27]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 57919248HCID 57919248, compound2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 57919202HCID 57919202, compoundYield 53%

Procedure

Using the method described in Example 17, 3-cyclopentyl-2-[6-oxo-4-(pyridin-3-yloxy)-6H-pyridazin-1-yl]-propionic acid (Intermediate 54) 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-(pyridin-3-yloxy)-6H-pyridazin-1-yl]-propionamide as an off-white solid (0.78 g, 53%); ES+-HRMS m/e calcd for C24H30N6O4 [M+H+] 467.2402 found 467.2399. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.05 (s, 3H), 1.06 (s, 3H), 1.11 (m, 1H), 1.26-1.75 (m, 8H), 1.92 (m, 1H), 2.29 (m, 1H), 3.89 (s, 2H), 4.67 (s, 1H), 5.48 (dd, J=4.4, J=11.0 Hz, 1H), 5.88 (d, J=2.8 Hz, 1H), 6.40 (d, J=2.3 Hz, 1H), 7.53 (d, J=2.3 Hz, 1H), 7.57 (dd, Jo=8.4, 4.7 Hz, 1H), 7.83 (ddd, Jo=8.4 Hz, Jm=2.8, 1.2 Hz, H), 8.17 (d, J=2.8 Hz, 1H), 8.58 (dd, Jo=4.7 Hz, Jm=1.2 Hz, 1H), 8.61 (d, Jm=2.8 Hz, H), 10.80 (s, 1H).

Sources & evidence

ORD record
ord-97b4b8fc5cee459f890cafc8972ab98f
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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