1-Methyl-3-aminopyrazole → 3-cyclopentyl-N-(1-methyl-1H-pyrazol-3-yl)-2-(6-oxo-6H-pyridazin-1-yl)-propionamide

HRID 2381499Notes

Reaction equation

HRID 2381499 reaction equation
[CH:1]1([CH2:6][CH:7]([N:11]2[C:16](=[O:17])[CH:15]=[CH:14][CH:13]=[N:12]2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:18][N:19]1[CH:23]=[CH:22][C:21]([NH2:24])=[N:20]1>>[CH:1]1([CH2:6][CH:7]([N:11]2[C:16](=[O:17])[CH:15]=[CH:14][CH:13]=[N:12]2)[C:8]([NH:24][C:21]2[CH:22]=[CH:23][N:19]([CH3:18])[N:20]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 1372541-Methyl-3-aminopyrazoleHCID 668753533-cyclopentyl-2-(6-oxo-6H-pyridazin-1-yl)-propionic acid

Product 1

HCID 579191433-cyclopentyl-N-(1-methyl-1H-pyrazol-3-yl)-2-(6-oxo-6H-pyridazin-1-yl)-propionamideYield 36%

Procedure

Using the method described in Example 78, Step 3, from 3-cyclopentyl-2-(6-oxo-6H-pyridazin-1-yl)-propionic acid (As prepared in Example 78, Step 2) and 1-methyl-1H-pyrazol-3-ylamine afforded 3-cyclopentyl-N-(1-methyl-1H-pyrazol-3-yl)-2-(6-oxo-6H-pyridazin-1-yl)-propionamide as a white solid (37.1 mg, 36%); ES+-HRMS m/e calcd for C16H21N5O2 [M+H+] 316.1768 found 316.1768. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.07 (br s, 1H), 1.24-1.36 (m, 1H), 1.36-1.49 (m, 2H), 1.49-1.74 (m, 5H), 1.93 (ddd, J=13.4, 8.6, 4.5 Hz, 1H), 2.18-2.31 (m, 1H), 3.73 (s, 3H), 5.51 (dd, J=10.7, 4.7 Hz, 1H), 6.35 (d, J=2.0 Hz, 1H), 6.94 (dd, J=9.5, 1.5 Hz, 1H), 7.42 (dd, J=9.5, 3.7 Hz, 1H), 7.53 (d, J=2.0 Hz, 1H), 7.99 (dd, J=3.7, 1.5 Hz, 1H), 10.72 (s, 1H).

Sources & evidence

ORD record
ord-e1d2c51eefca480f895251fe35bacdb7
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

Loading…