5-Cyclopropyl-1,3,4-thiadiazol-2-amine → 5-Chloro-N-{2-[4-(5-cyclopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-ethyl}-2-methoxy-benzamide

HRID 2266403Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:22]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1)=[O:8].[CH:25]1([C:28]2[S:32][C:31]([NH2:33])=[N:30][N:29]=2)[CH2:27][CH2:26]1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:22]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](=[O:20])(=[O:19])[NH:33][C:31]2[S:32][C:28]([CH:25]3[CH2:27][CH2:26]3)=[N:29][N:30]=2)=[CH:14][CH:13]=1)=[O:8]

Participants

Conditions

Temperature: 115 °C

Procedure

1.1 g 4-[2-(5-Chloro-2-methoxy-benzoylamino)-ethyl]-benzenesulfonyl chloride, 483 mg 5-Cyclopropyl-[1,3,4]thiadiazol-2-ylamine and 35.0 mg 4-dimethylaminopyridine were dissolved in 5 ml pyridine and stirred under microwave irradiation at 115° C. for two hours. The pyridine was removed in vacuo and the residue coevaporated three times with portions of 20 ml toluene. The residue was purified by RP-HPLC to obtain 590 mg 5-Chloro-N-{2-[4-(5-cyclopropyl-[1,3,4]thiadiazol-2-ylsulfamoyl)-phenyl]-ethyl}-2-methoxy-benzamide.

Workup

customThe pyridine was removed in vacuo
customThe residue was purified by RP-HPLC

Sources & evidence

ORD record: ord-f84d6dbf280d4bed969e5300335db827
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858647B2

Reaction notes

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