Cyclopropanesulfonyl chloride → HCID 44217995, compound

HRID 1669713Notes

Reaction equation

HRID 1669713 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.[CH:20]1([S:23](Cl)(=[O:25])=[O:24])[CH2:22][CH2:21]1>N1C=CC=CC=1>[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:23]([CH:20]3[CH2:22][CH2:21]3)(=[O:25])=[O:24])[N:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2760919Cyclopropanesulfonyl chlorideHCID 44217679HCID 44217679, compound

Product 1

HCID 44217995HCID 44217995, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N2-(5-Methyl-furan-2-ylmethyl)-quinoline-2,5-diamine (200 mg, 0.79 mmol) was dissolved in 2 mL pyridine and cyclopropane sulfonylchloride (118 mg, 0.79 mmol) was added. The reaction mixture was stirred at room temperature overnight and quenched by addition of 50 mL water and acetic acid until pH 5. The mixture was extracted three times with ethyl acetate (50 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->50:50 gradient). The title compound was obtained as a yellow oil (234 mg, 78%), MS: m/e=358.4 (M+H+).

Workup

  1. customquenched by addition of 50 mL water and acetic acid until pH 5
  2. extractionThe mixture was extracted three times with ethyl acetate (50 mL each)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->50:50 gradient)

Sources & evidence

ORD record
ord-43fab9c78a934ebba138b425f108bd51
Source dataset
uspto-grants-2011_08
Patent number
US07989628B2

Reaction notes

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