2-Aminothiazole → HCID 44463247, compound

HRID 2381410Notes

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

Participants

Reactant 2

HCID 21552-Aminothiazole

HCID 46223054HCID 46223054, compound2×

Product 1

HCID 44463247HCID 44463247, compoundYield 45.3%

Procedure

Using the method described in Example 1, 3-cyclopentyl-2-(6-oxo-4-phenoxy-6H-pyridazin-1-yl)-propionic acid (Intermediate 19) and thiazol-2-ylamine afforded 3-cyclopentyl-2-(6-oxo-4-phenoxy-6H-pyridazin-1-yl)-N-thiazol-2-yl-propionamide as a white solid (53.9 mg, 45.3%); ES+-HRMS m/e calcd for C21H22N4O3S [M+H+] 411.1486, found 411.1485. 1H-NMR (300 MHz, DMSO-d6) δ ppm 1.02-1.87 (m, 9H), 1.97 (m, 1H), 2.26 (m, 1H), 5.54 (dd, J=4.4, J=10.7 Hz, 1H), 5.57 (d, J=2.7 Hz, 1H), 7.23 (d, J=3.6 Hz, 1H), 7.30 (d, J=7.5 Hz, 2H), 7.37 (t, J=7.5 Hz, 1H), 7.49 (d, J=3.6 Hz, 1H), 7.53 (t, J=7.5 Hz, 2H), 8.16 (d, J=2.7 Hz, 1H), 12.55 (s, 1H).

Sources & evidence

ORD record: ord-044db566515643e1bdfc47ad3ade1a9a
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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