2-[4-(biphenyl-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentylpropionic acid → HCID 57919181, compound

HRID 2381430Notes

Reaction equation

HRID 2381430 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]1[CH:9]=[N:10][N:11]([CH:15]([CH2:19][CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[C:16](O)=[O:17])[C:12](=[O:14])[CH:13]=1.[NH2:31][C:32]1[CH:36]=[CH:35][N:34]([CH2:37][C:38]([CH3:41])([OH:40])[CH3:39])[N:33]=1>>[C:1]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]1[CH:9]=[N:10][N:11]([CH:15]([CH2:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24]2)[C:16]([NH:31][C:32]2[CH:36]=[CH:35][N:34]([CH2:37][C:38]([OH:40])([CH3:41])[CH3:39])[N:33]=2)=[O:17])[C:12](=[O:14])[CH:13]=1

Participants

3

Reactant 2

HCID 579191692-[4-(biphenyl-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentylpropionic acid2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 57919181HCID 57919181, compoundYield 50%

Procedure

Using the method described in Example 17, 2-[4-(biphenyl-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid (Intermediate 37) and 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (Intermediate 1) afforded 2-[4-(biphenyl-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamide as a white solid (0.74 g, 50%); ES+-HRMS m/e calcd for C31H35N5O4 [M+H+] 542.2762 found 542.2759. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.02 (m, 1H), 1.04 (s, 3H), 1.05 (s, 3H), 1.26 (m, 1H), 1.36-1.66 (m, 7H), 1.88 (m, 1H), 2.15 (m, 1H), 3.88 (s, 2H), 4.66 (s, 1H), 5.37 (dd, J=4.4, J=11.0 Hz, 1H), 5.62 (d, J=2.9 Hz, 1H), 6.37 (d, J=2.3 Hz, 1H), 7.29-7.36 (m, 1H), 7.37-7.43 (m, 3H), 7.44-7.60 (m, 6H), 7.97 (d, J=2.9 Hz, 1H), 10.73 (s, 1H).

Sources & evidence

ORD record
ord-fe8a3eb5d0d348ef9a5f4c087c38383e
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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