5-Amino-3-methyl-1,2,4-thiadiazole → HCID 57919148, compound

HRID 2381411Notes

Reaction equation

HRID 2381411 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.[CH3:25][C:26]1[N:30]=[C:29]([NH2:31])[S:28][N:27]=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:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:13]=[N:12]2)[C:8]([NH:31][C:29]2[S:28][N:27]=[C:26]([CH3:25])[N:30]=2)=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 3506395-Amino-3-methyl-1,2,4-thiadiazoleHCID 46223054HCID 46223054, compound2×

Product 1

HCID 57919148HCID 57919148, compoundYield 12.1%

Procedure

Using the method described in Example 1, 3-cyclopentyl-2-(6-oxo-4-phenoxy-6H-pyridazin-1-yl)-propionic acid (Intermediate 19) and 3-methyl-[1,2,4]thiadiazol-5-ylamine afforded 3-cyclopentyl-N-(3-methyl-[1,2,4]thiadiazol-5-yl)-2-(6-oxo-4-phenoxy-6H-pyridazin-1-yl)-propionamide as a white solid (23.8 mg, 12.1%); ES+-HRMS m/e calcd for C21H23N5O3S [M+H+] 426.1595, found 426.1594. 1H-NMR (300 MHz, DMSO-d6) δ ppm 1.01-1.77 (m, 9H), 2.03 (m, 1H), 2.27 (m, 1H), 2.44 (s, 3H), 5.57 (dd, J=4.5, J=10.6 Hz, 1H), 5.76 (d, J=2.8 Hz, 1H), 7.30 (d, J=7.5 Hz, 2H), 7.37 (t, J=7.5 Hz, 1H), 7.54 (t, J=7.5 Hz, 2H), 8.17 (d, J=2.8 Hz, 1H), 13.26 (s, 1H).

Sources & evidence

ORD record
ord-914dd2c210754e889cec4ab03fc2a1ea
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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