Water → 7-Methoxy-4-(5-(3-phenylureido)thiophen-2-ylsulfanyl)quinoline-6-carboxamide

HRID 1010236Notes

Reaction equation

HRID 1010236 reaction equation
[NH2:1][C:2]1[S:6][C:5]([S:7][C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:21][CH3:22])=[C:15]([C:18]([NH2:20])=[O:19])[CH:16]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:23]1([N:29]=[C:30]=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[CH3:22][O:21][C:14]1[CH:13]=[C:12]2[C:17]([C:8]([S:7][C:5]3[S:6][C:2]([NH:1][C:30]([NH:29][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:31])=[CH:3][CH:4]=3)=[CH:9][CH:10]=[N:11]2)=[CH:16][C:15]=1[C:18]([NH2:20])=[O:19]

Participants

7

Reactant 3

HCID 962WaterHCID 7672Phenyl isocyanateHCID 229362694-(5-Aminothiophen-2-ylsulfanyl)-7-methoxyquinoline-6-carboxamide

Product 1

HCID 229369217-Methoxy-4-(5-(3-phenylureido)thiophen-2-ylsulfanyl)quinoline-6-carboxamideYield 37.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

4-(5-Aminothiophen-2-ylsulfanyl)-7-methoxyquinoline-6-carboxamide (49.0 mg, 0.150 mmol) and phenyl isocyanate (19.6 mg, 0.165 mmol) were stirred in dimethylformamide (1 ml) at room temperature for 2 hours. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was suspended in ethyl acetate and diluted with hexane, and then the crystals were filtered out, washed with hexane and blow-dried to obtain the title compound (25.0 mg, 0.056 mmol, 37%) as light yellow crystals.

Workup

  1. washthe organic layer was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe drying agent was filtered off
  4. distillationthe filtrate was distilled off under reduced pressure
  5. customThe obtained crude product
  6. filtrationthe crystals were filtered out
  7. washwashed with hexane
  8. customblow-dried

Sources & evidence

ORD record
ord-98a3e8fbcf9d44c8855f5d8138a40a3e
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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