2-Aminothiazole → 3-cyclopentyl-2-(6-oxo-6H-pyridazin-1-yl)-N-thiazol-2-yl-propionamide

HRID 2381494Notes

Reaction equation

HRID 2381494 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.[S:18]1[CH:22]=[CH:21][N:20]=[C:19]1[NH2:23]>>[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:23][C:19]2[S:18][CH:22]=[CH:21][N:20]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 21552-AminothiazoleHCID 668753533-cyclopentyl-2-(6-oxo-6H-pyridazin-1-yl)-propionic acid

Product 1

HCID 579192673-cyclopentyl-2-(6-oxo-6H-pyridazin-1-yl)-N-thiazol-2-yl-propionamideYield 29%

Procedure

Using the method described in Example 78, Step 3,3-cyclopentyl-2-(6-oxo-6H-pyridazin-1-yl)-propionic acid (prepared as in Example 78, Step 2) and thiazol-2-ylamine afforded 3-cyclopentyl-2-(6-oxo-6H-pyridazin-1-yl)-N-thiazol-2-yl-propionamide as a white solid (39.9 mg, 29%); ES+-HRMS m/e calcd for C15H18N4O2S [M+H+] 319.1223 found 319.1223. 1H-NMR (300 MHz, DMSO-d6) δ ppm 1.00-1.75 (m, 9H), 1.99 (m, 1H, CH), 2.28 (m, 1H), 5.60 (dd, J=4.5, J=10.3 Hz, 1H), 6.98 (dd, Jo=9.4 Hz, Jm=1.5 Hz, 1H), 7.23 (d, J=3.6 Hz, 1H), 7.45 (dd, Jo=9.4, Jo=3.6 Hz, 1H), 7.49 (d, J=3.6 Hz, 1H), 8.02 (dd, Jo=3.6 Hz, Jm=1.5 Hz, 1H), 12.58 (s, 1H).

Sources & evidence

ORD record
ord-f7d0d54bee7347229bbdb1d847cbb245
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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