Hydrochloric Acid → HCID 56601184, compound

HRID 1619599Notes

Reaction equation

[CH3:1][N:2]1[C:6]([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:5][CH:4]=[N:3]1.C(=O)([O-])[O-].[K+].[K+].[C:26]([C:28]1[CH:29]=[C:30]([S:35]([NH:38][C:39]2[S:43][N:42]=[CH:41][N:40]=2)(=[O:37])=[O:36])[CH:31]=[CH:32][C:33]=1F)#[N:27].Cl>CN(C)C=O>[C:26]([C:28]1[CH:29]=[C:30]([S:35]([NH:38][C:39]2[S:43][N:42]=[CH:41][N:40]=2)(=[O:37])=[O:36])[CH:31]=[CH:32][C:33]=1[O:13][C:12]1[CH:11]=[CH:10][C:9]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:8][C:7]=1[C:6]1[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=1)#[N:27]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 3-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-ol (Preparation 28, 44.1 mg, 0.176 mmol) and potassium carbonate (30.4 mg, 0.22 mmol) in N,N-dimethylformamide (1 mL) was added 3-cyano-4-fluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (Preparation 47, 50.0 mg, 0.176 mmol) and the reaction mixture was stirred at 100° C. After stirring for 24 hours, the reaction mixture was cooled to room temperature. A 1M aqueous solution of hydrogen chloride (10 mL) was added to the reaction mixture and the mixture was extracted with dichloromethane (3×10 mL). The combined organic layer was concentrated in vacuo to obtain the title compound (90 mg, 99%).

Workup

stirringAfter stirring for 24 hours
temperaturethe reaction mixture was cooled to room temperature
extractionthe mixture was extracted with dichloromethane (3×10 mL)
concentrationThe combined organic layer was concentrated in vacuo

Sources & evidence

ORD record: ord-d899534f5f844d4689ce8a48c4735b9f
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772293B2

Reaction notes

Loading…