Potassium Carbonate → HCID 24962321, compound

HRID 72684Notes

Reaction equation

HRID 72684 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:9]=[C:10]([S:14]([NH2:17])(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=2)=[C:6]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[N:5]=[C:4]([C:25]([F:28])([F:27])[F:26])[N:3]=1.[OH:29][C:30]1[CH:40]=[CH:39][C:33]([C:34]([NH:36][O:37][CH3:38])=[O:35])=[CH:32][C:31]=1[O:41][CH3:42].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:42][O:41][C:31]1[CH:32]=[C:33]([CH:39]=[CH:40][C:30]=1[O:29][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([S:14]([NH2:17])(=[O:16])=[O:15])[CH:9]=2)=[C:6]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[N:5]=[C:4]([C:25]([F:28])([F:27])[F:26])[N:3]=1)[C:34]([NH:36][O:37][CH3:38])=[O:35]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 58089378HCID 58089378, compoundHCID 60140024HCID 60140024, compound

Product 1

HCID 24962321HCID 24962321, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of 3-[4-chloro-6-(4-fluorophenyl)-2-(trifluoromethyl)pyrimidin-5-yl]benzenesulfonamide (0.15 g, 0.35 mmol), 4-hydroxy-N,3-dimethoxybenzamide (0.102 g, 0.52 mmol) and potassium carbonate (0.52 mmol) in acetonitrile (3 ml) were heated to reflux (65° C.) for 2 hours. Subsequently the reaction mixture was poured onto ice-cold water, extracted with dichloromethane (50 ml) and washed with brine. Evaporation of the organic layer furnished a crude material, which was purified by column chromatography; elution with 2% MeOH in dichloromethane furnished the required compound. 1H-NMR (DMSO-d6) δ: 3.73 (s, 3H), 3.79 (s, 3H), 7.16-7.20 (m, 2H), 7.37 (d, 1H), 7.41-7.45 (m, 5H), 7.53 (s, 1H), 7.62-7.63 (d, 2H), 7.85 (d, 1H), 7.89 (s, 1H). 11.9 (s, 1H); MS m/z: 593 (M++1).

Workup

  1. temperaturewere heated
  2. additionSubsequently the reaction mixture was poured onto ice-cold water
  3. extractionextracted with dichloromethane (50 ml)
  4. washwashed with brine
  5. customEvaporation of the organic layer
  6. customfurnished a crude material, which
  7. customwas purified by column chromatography
  8. washelution with 2% MeOH in dichloromethane

Sources & evidence

ORD record
ord-453eb2f7bf99405d819849786b15e304
Source dataset
uspto-grants-2014_09
Patent number
US08828999B2

Reaction notes

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