HCID 57919111, compound → HCID 44466926, compound

HRID 2381419Notes

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[O:25][CH3:26])[CH:13]=[N:12]2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:27][C:28]1[CH:32]=[CH:31][N:30]([CH2:33][C:34]([CH3:37])([OH:36])[CH3:35])[N:29]=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[O:25][CH3:26])[CH:13]=[N:12]2)[C:8]([NH:27][C:28]2[CH:32]=[CH:31][N:30]([CH2:33][C:34]([OH:36])([CH3:35])[CH3:37])[N:29]=2)=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 57919111HCID 57919111, compound2×

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

Product 1

HCID 44466926HCID 44466926, compoundYield 65%

Procedure

Using the method described in Example 11, 3-cyclopentyl-2-[4-(2-methoxy-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (Intermediate 24) 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-[4-(2-methoxy-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionamide as a white solid (83.8 mg, 65%); ES+-HRMS m/e calcd for C26H33N5O5 [M+H+] 496.2555 found 496.2552. 1H-NMR (300 MHz, DMSO-d6) δ ppm 1.04 (s, 3H), 1.06 (s, 3H), 1.09 (m, 1H), 1.21-1.74 (m, 8H), 1.91 (m, 1H), 2.27 (m, 1H), 3.80 (s, 3H), 3.89 (s, 2H), 4.68 (s, 1H), 5.45 (dd, J=4.2, J=11.2 Hz, 1H), 5.56 (d, J=2.7 Hz, 1H), 6.39 (d, J=2.1 Hz, 1H), 7.00-7.11 (m, 1H), 7.20-7.31 (m, 2H), 7.31-7.41 (m, 1H), 7.52 (d, J=2.1 Hz, 1H), 8.12 (d, J=2.7 Hz, 1H), 10.83 (s, 1H).

Sources & evidence

ORD record: ord-4b7c8f73975d4a49b3a1788f989d1482
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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