Potassium Carbonate → HCID 131728509, compound

HRID 1927531Notes

Reaction equation

HRID 1927531 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([CH3:10])[C:7](Br)=[C:6]([S:12](=[O:22])(=[O:21])[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[OH:20])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]([CH3:10])[C:7]2[O:20][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[NH:13][S:12](=[O:22])(=[O:21])[C:6]=2[CH:5]=1)=[O:23]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 68426884HCID 68426884, compound

Product 1

HCID 131728509HCID 131728509, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 155a (2.0 g, 4.99 mmol) and anhydrous potassium carbonate (1.38 g, 9.99 mmol) in dry DMF (25 mL) was heated at 95° C. for 20 h. The reaction mixture was concentrated treated with water, 10% aqueous HCl solution and extracted with 1-butanol. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, 2.5% methanol/chloroform) to obtain the title compound. Yield: 0.9 g, (56.4%) 1H NMR (DMSO-d6): δ 2.4 (s, 3H, CH3), 3.9 (s, 3H, OCH3), 7.1 (m, 1H, Ar), 7.2 (m, 2H, Ar), 7.48 (m, 1H, Ar), 8.1 (s, 1H, Ar), 11.1 (s, 1H, NH); MS: m/e (ES+) 320 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiontreated with water, 10% aqueous HCl solution
  3. extractionextracted with 1-butanol
  4. washThe organic layer was washed with water, brine
  5. customdried
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-90368cdf10d649ea9479a768a2a25422
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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