Cyclopropanesulfonyl chloride → Cyclopropanesulfonic acid[2-((r)-indan-1-ylamino)-quinolin-5-yl]-amide

HRID 1671553Notes

Reaction equation

HRID 1671553 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:17]([NH2:21])=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH:22]1([S:25](Cl)(=[O:27])=[O:26])[CH2:24][CH2:23]1>N1C=CC=CC=1>[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[NH:21][S:25]([CH:22]3[CH2:24][CH2:23]3)(=[O:27])=[O:26])[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2760919Cyclopropanesulfonyl chlorideHCID 44219082(R)-N2-Indan-1-yl-quinoline-2,5-diamine

Product 1

HCID 44219083Cyclopropanesulfonic acid[2-((r)-indan-1-ylamino)-quinolin-5-yl]-amide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(R)—N2-Indan-1-yl-quinoline-2,5-diamine (200 mg, 0.73 mmol) was dissolved in 2 mL pyridine and cyclopropane sulfonylchloride (102 mg, 0.73 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 brown solid (160 mg, 58%), MS: m/e=380.4 (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-65e04d918b1b4d8b97950ef793897985
Source dataset
uspto-grants-2011_08
Patent number
US07994324B2

Reaction notes

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