Acetic Acid → (+/-)-5-(7-Chloro-2-(1,3,4-thiadiazolylthio)-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-yl)-1-methyl-2,4(1H,3H)-pyrimidinedione

HRID 324508Notes

Reaction equation

Cl[C:2]1[S:3][C:4]2[CH:11]=[CH:10][C:9]3[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:8]=3[CH:7]([C:17]3[C:18](=[O:25])[NH:19][C:20](=[O:24])[N:21]([CH3:23])[CH:22]=3)[C:5]=2[N:6]=1.[SH:26][C:27]1[S:28][CH:29]=[N:30][N:31]=1.[H-].[Na+].C(O)(=O)C>CN(C)C=O.O>[Cl:16][C:13]1[CH:14]=[CH:15][C:8]2[CH:7]([C:17]3[C:18](=[O:25])[NH:19][C:20](=[O:24])[N:21]([CH3:23])[CH:22]=3)[C:5]3[N:6]=[C:2]([S:26][C:27]4[S:28][CH:29]=[N:30][N:31]=4)[S:3][C:4]=3[CH:11]=[CH:10][C:9]=2[CH:12]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a mixture of the product from example 44 step (viii) (0.20 g) and 2-mercapto-1,3,4-thiadiazole (0.120 g) in dry dimethylformamide (2 ml) was added 60% sodium hydride (0.041 g). The mixture was stirred for 16 h then heated at 55° C. for 24 h. The reaction mixture was diluted with water and neutralised by the addition of acetic acid. The aqueous was extracted with dichloromethane and the combined organic extracts were dried (MgSO4). The solvent was removed under reduced pressure and the residue purified by flash chromatography eluting with dichloromethane/5% ethanol.

Workup

extractionThe aqueous was extracted with dichloromethane
dry with materialthe combined organic extracts were dried (MgSO4)
customThe solvent was removed under reduced pressure
customthe residue purified by flash chromatography
washeluting with dichloromethane/5% ethanol

Sources & evidence

ORD record: ord-41069b28a3854e989e612c79d92963e9
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218376B1

Reaction notes

Loading…