1,3,4-Thiadiazole, 2-amino-5-methyl- → HCID 57919273, compound

HRID 2381412Notes

Reaction equation

HRID 2381412 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[S:30][C:29]([NH2:31])=[N: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:30][C:26]([CH3:25])=[N:27][N:28]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 669491,3,4-Thiadiazole, 2-amino-5-methyl-HCID 46223054HCID 46223054, compound2×

Product 1

HCID 57919273HCID 57919273, compoundYield 31.4%

Procedure

Using the method described in Example 1, 3-cyclopentyl-2-(6-oxo-4-phenoxy-6H-pyridazin-1-yl)-propionic acid (Intermediate 19) and 5-methyl-[1,3,4]thiadiazol-2-ylamine afforded 3-cyclopentyl-N-(5-methyl-[1,3,4]thiadiazol-2-yl)-2-(6-oxo-4-phenoxy-6H-pyridazin-1-yl)-propionamide as a white solid (60.1 mg, 31.4%); ES+-HRMS m/e calcd for C21H23N5O3S [M+Na+] 448.1414, found 448.1413. 1H-NMR (300 MHz, DMSO-d6) δ ppm 1.01-1.77 (m, 9H), 1.96 (m, 1H), 2.26 (m, 1H), 2.58 (s, 3H), 5.52 (dd, J=4.2, J=10.6 Hz, 1H), 5.73 (d, J=2.7 Hz, 1H), 7.28 (d, J=7.5 Hz, 2H), 7.35 (t, J=7.5 Hz, 1H), 7.52 (t, J=7.5 Hz, 2H), 8.14 (d, J=2.7 Hz, 1H), 12.82 (s, 1H).

Sources & evidence

ORD record
ord-4dc9c5e28f564bb493e22fb026a254d0
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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