HCID 57919284, compound → HCID 57919235, compound

HRID 2381431Notes

Reaction equation

HRID 2381431 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[CH3:25])[CH:13]=[N:12]2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:26][C:27]1[CH:31]=[CH:30][N:29]([CH2:32][C:33]([CH3:36])([OH:35])[CH3:34])[N:28]=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[CH3:25])[CH:13]=[N:12]2)[C:8]([NH:26][C:27]2[CH:31]=[CH:30][N:29]([CH2:32][C:33]([OH:35])([CH3:34])[CH3:36])[N:28]=2)=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 57919284HCID 57919284, compound2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 57919235HCID 57919235, compoundYield 58%

Procedure

Using the method described in Example 17, 3-cyclopentyl-2-(6-oxo-4-o-tolyloxy-6H-pyridazin-1-yl)-propionic acid (Intermediate 41) 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-o-tolyloxy-6H-pyridazin-1-yl)-propionamide as a white solid (0.86 g, 58%); ES+-HRMS m/e calcd for C26H33N5O4 [M+H+] 480.2606 found 480.2605. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.05 (s, 3H), 1.06 (s, 3H), 1.09 (m, 1H), 1.27-1.75 (m, 8H), 1.92 (m, 1H), 2.16 (s, 3H), 2.27 (m, 1H), 3.89 (s, 2H), 4.67 (s, 1H), 5.45 (dd, J=4.3, J=10.9 Hz, 1H), 5.56 (d, J=2.8 Hz, 1H), 6.40 (d, J=2.3 Hz, 1H), 7.21 (dd, Jo=7.5 Hz, Jm=1.3 Hz, 1H), 7.28 (td, Jo=7.5 Hz, Jm=1.3 Hz, 1H), 7.34 (td, Jo=7.5 Hz, Jm=1.3 Hz, 1H), 7.41 (d, Jo=7.5 Hz, 1H), 7.53 (d, J=2.3 Hz, 1H), 8.15 (d, J=2.8 Hz, 1H), 10.80 (s, 1H).

Sources & evidence

ORD record
ord-31e3c9715e53499c9fac220ecdb48ae5
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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