1-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol → 3-cyclopentyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-2-(4-methoxy-6-oxo-6H-pyridazin-1-yl)-propionamide

HRID 2381498Notes

Reaction equation

HRID 2381498 reaction equation
[CH:1]1([CH2:6][CH:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][CH3:19])[CH:13]=[N:12]2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:20][C:21]1[CH:25]=[CH:24][N:23]([CH2:26][C:27]([CH3:30])([OH:29])[CH3:28])[N:22]=1>>[CH:1]1([CH2:6][CH:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][CH3:19])[CH:13]=[N:12]2)[C:8]([NH:20][C:21]2[CH:25]=[CH:24][N:23]([CH2:26][C:27]([OH:29])([CH3:28])[CH3:30])[N:22]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol2×HCID 668754403-cyclopentyl-2-(4-methoxy-6-oxo-6H-pyridazin-1-yl)-propionic acid

Product 1

HCID 579193133-cyclopentyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-2-(4-methoxy-6-oxo-6H-pyridazin-1-yl)-propionamideYield 29%

Procedure

Using the method described in Example 80, Step 3,3-cyclopentyl-2-(4-methoxy-6-oxo-6H-pyridazin-1-yl)-propionic acid (as prepared in Example 80, Step 2) 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-methoxy-6-oxo-6H-pyridazin-1-yl)-propionamide as an off-white solid (45.1 mg, 29%); ES+-HRMS m/e calcd for C20H29N5O4 [M+H+] 404.2293 found 404.2292. 1H-NMR (300 MHz, DMSO-d6) δ ppm 1.04 (m, 1H), 1.05 (s, 3H), 1.06 (s, 3H), 1.18-1.77 (m, 8H), 1.91 (m, 1H), 2.26 (m, 1H), 3.81 (s, 3H), 3.89 (s, 2H), 4.67 (s, 1H), 5.46 (dd, J=4.1, J=11.3 Hz, 1H), 6.29 (d, J=2.7 Hz, 1H), 6.39 (s, 1H), 7.52 (s, 1H), 7.84 (d, J=2.7 Hz, 1H), 10.73 (s, 1H).

Sources & evidence

ORD record
ord-ad2d7905caba4e3fab66436c59254612
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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