Water → HCID 24987863, compound

HRID 1170101Notes

Reaction equation

HRID 1170101 reaction equation
[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]2[CH:18]=[CH:17][C:16]3[C:15]([NH2:19])=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[C:29]1([S:35](Cl)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.O>CN(C)C=O>[CH3:1][C:2]1[O:6][C:5]([CH2:7][NH:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[NH:19][S:35]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:37])=[O:36])[N:10]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 44217679HCID 44217679, compound

Product 1

HCID 24987863HCID 24987863, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N2-(5-Methyl-furan-2-ylmethyl)-quinoline-2,5-diamine (example 26, step A+B, 200 mg, 0.791 mmol) was dissolved in 2 mL N,N-dimethylformamide. N,N-Diisopropyl ethyl amine (104 mg; 0.806 mmol) and benzenesulfonyl chloride (155 mg, 0.876 mmol) were added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into 50 mL water and extracted three times with ethyl acetate (50 mL each). The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate/methanol 100:0:0->0:90:10 gradient). The title compound was obtained as a yellow solid (130 mg, 42%), MS: m/e=394.1 (M+H+).

Workup

  1. extractionextracted three times with ethyl acetate (50 mL each)
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue purified by flash chromatography on silica gel (cyclohexane/ethyl acetate/methanol 100:0:0->0:90:10 gradient)

Sources & evidence

ORD record
ord-59b914f336bd4de598434f4447efd021
Source dataset
uspto-grants-2010_11
Patent number
US07825253B2

Reaction notes

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