HCID 57919130, compound → HCID 57919131, compound

HRID 2381425Notes

Reaction equation

HRID 2381425 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]=[C:21]([F:25])[CH:20]=3)[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]=[C:21]([F:25])[CH:20]=3)[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 57919130HCID 57919130, compound2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 57919131HCID 57919131, compoundYield 53%

Procedure

Using the method described in Example 17, 3-cyclopentyl-2-[4-(3-fluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (Intermediate 42) and 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (Intermediate 1) afforded 3-cyclopentyl-2-[4-(3-fluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamide as a white solid (0.74 g, 53%); ES+-HRMS m/e calcd for C25H30N5O4F [M+H+] 484.2355 found 484.2356. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.05 (s, 3H), 1.06 (s, 3H), 1.10 (m, 1H), 1.27-1.75 (m, 8H), 1.92 (m, 1H), 2.28 (m, 1H), 3.89 (s, 2H), 4.67 (s, 1H), 5.48 (dd, J=4.3, J=10.9 Hz, 1H), 5.88 (d, J=2.9 Hz, 1H), 6.40 (d, J=2.3 Hz, 1H), 7.17 (dd, Jm=2.3 Hz, Jo=8.3 Hz, 1H), 7.22 (td, Jm=2.3 Hz, Jo=8.3 Hz, 3JF=8.3 Hz, 1H), 7.31 (dt, Jm=2.3 Hz, 3JF=9.9 Hz, 1H), 7.53 (d, J=2.3 Hz, 1H), 7.57 (dt, Jo=8.3 Hz, 4JF=6.9 Hz, 1H), 8.13 (d, J=2.9 Hz, 1H), 10.80 (s, 1H).

Sources & evidence

ORD record
ord-e11a1a46d7474f92a3fd62872cc9d061
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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