Potassium Carbonate → 3-Cyano-4-[(3-pyridazin-4-ylbiphenyl-4-yl)oxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

HRID 1619595Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:10]=[CH:11][C:12]=2[OH:13])=[CH:3][N:2]=1.[C:20]([C:22]1[CH:23]=[C:24]([S:29]([NH:32][C:33]2[S:37][N:36]=[CH:35][N:34]=2)(=[O:31])=[O:30])[CH:25]=[CH:26][C:27]=1F)#[N:21].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:20]([C:22]1[CH:23]=[C:24]([S:29]([NH:32][C:33]2[S:37][N:36]=[CH:35][N:34]=2)(=[O:31])=[O:30])[CH:25]=[CH:26][C:27]=1[O:13][C:12]1[CH:11]=[CH:10][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][C:7]=1[C:4]1[CH:5]=[CH:6][N:1]=[N:2][CH:3]=1)#[N:21]

Participants

Conditions

Temperature: 90 °C

Procedure

3-Pyridazin-4-ylbiphenyl-4-ol (Preparation 4, 50 mg, 0.2 mmol) and 3-cyano-4-fluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (Preparation 47, 50 mg, 0.2 mmol) were dissolved in dimethylsulfoxide (2 mL). Potassium carbonate (83 mg, 0.6 mmol) was added and the reaction heated to 90° C. for 16 hours. The crude material was then purified by reverse phase column chromatography (ISCO™, 4 g, C18, 20:1 water:acetonitrile to 3:2 water acetonitrile). The appropriate fractions were combined and concentrated in vacuo to afford the title compound as an off white solid (25 mg, 24%).

Workup

customThe crude material was then purified by reverse phase column chromatography (ISCO™, 4 g, C18, 20:1 water:acetonitrile to 3:2 water acetonitrile)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7c12fe9a2fc8458ea1001bb864548439
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772293B2

Reaction notes

Loading…