HCID 57919124, compound → HCID 44464554, compound

HRID 2381415Notes

Reaction equation

HRID 2381415 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]([O:25][CH3:26])[CH:20]=3)[CH:13]=[N:12]2)[C:8](O)=[O:9])[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]=[C:21]([O:25][CH3:26])[CH:20]=3)[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:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 57919124HCID 57919124, compound2×HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×

Product 1

HCID 44464554HCID 44464554, compoundYield 10.1%

Procedure

Using the method described in Example 1, 3-cyclopentyl-2-[4-(3-methoxy-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (Intermediate 25) 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-(3-methoxy-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionamide as an off-white solid (14.6 mg, 10.1%); ES+-HRMS m/e calcd for C26H33N5O5 [M+Na+] 518.2374 found 518.2378. 1H-NMR (300 MHz, DMSO-d6) δ ppm 1.05 (s, 3H), 1.06 (s, 3H), 1.09 (m, 1H), 1.21-1.74 (m, 8H), 1.91 (m, 1H), 2.27 (m, 1H), 3.78 (s, 3H), 3.89 (s, 2H), 4.67 (s, 1H), 5.45 (m., 1H), 5.78 (br.s., 1H), 6.40 (s, 1H), 6.81-6.98 (m, 3H), 7.37-7.49 (m, 1H), 7.52 (d, J=2.1 Hz, 1H), 8.11 (d, J=2.4 Hz, 1H), 10.81 (s, 1H).

Sources & evidence

ORD record
ord-777d9c31d0024977a879ddfdc3a84fc1
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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