Potassium Carbonate → HCID 56599016, compound

HRID 2283617Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=1[OH:18].[C:19]([C:21]1[CH:22]=[C:23]([S:28]([NH:31][C:32]2[S:36][N:35]=[CH:34][N:33]=2)(=[O:30])=[O:29])[CH:24]=[CH:25][C:26]=1F)#[N:20].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:19]([C:21]1[CH:22]=[C:23]([S:28]([NH:31][C:32]2[S:36][N:35]=[CH:34][N:33]=2)(=[O:30])=[O:29])[CH:24]=[CH:25][C:26]=1[O:18][C:9]1[CH:10]=[CH:11][C:12]([C:14]([F:15])([F:17])[F:16])=[CH:13][C:8]=1[C:7]1[CH:6]=[CH:5][N:4]=[N:3][C:2]=1[CH3:1])#[N:20]

Participants

Conditions

Temperature: 90 °C

Procedure

2-(3-Methylpyridazin-4-yl)-4-(trifluoromethyl)phenol (Preparation 44, 100 mg, 0.38 mmol) and 3-cyano-4-fluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (Preparation 39, 108 mg, 0.38 mmol) were dissolved in dimethylsulfoxide (2 mL). Potassium carbonate (157 mg, 1.14 mmol) was added and the reaction mixture was heated to 90° C. for 4 hours. The reaction mixture was cooled and the crude material purified by reverse phase column chromatography (ISCO™ Companion, C18 silica, 5% to 60% acetonitrile in water gradient elution) to afford the title compound as an off-white solid (130 mg).

Workup

temperatureThe reaction mixture was cooled
customthe crude material purified by reverse phase column chromatography (ISCO™ Companion
washC18 silica, 5% to 60% acetonitrile in water gradient elution)

Sources & evidence

ORD record: ord-b833e171311546288fddb9e239887254
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145407B2

Reaction notes

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