Piperidine → HCID 69545146, compound

HRID 2213678Notes

Reaction equation

HRID 2213678 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)(=[O:4])=[O:3].[CH2:15]([NH:17][C:18]([C:20]([C:22]1[NH:23][CH:24]=[CH:25][CH:26]=1)=O)=[O:19])[CH3:16].N1CCCCC1>ClCCl>[NH2:1][S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]2=[C:20]([C:22]1[NH:23][CH:24]=[CH:25][CH:26]=1)[C:18]([NH:17][CH2:15][CH3:16])=[O:19])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 101982322-Oxoindoline-5-sulfonamideHCID 21957685HCID 21957685, compound

Product 1

HCID 69545146HCID 69545146, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Alternatively, a mixture of 5-aminosulfonylindolin-2-one (0.22 g, 1.0 mmol), 2-(ethylamino)carbonylcarbonylpyrrole (0.33 g, 2.0 mmol) and piperidine (0.2 mL, 2.0 mmol) was irradiated in a microwave at 160° C. for 5 minutes. The reaction mixture was dissolved in dichloromethane (25 mL). The resulting mixture was washed with 0.2 N HCl (25 mL) and saturated sodium bicarbonate (25 mL), dried (magnesium sulfate) and concentrated. Chromatography on SiO2 (10 g) using hexane/ethyl acetate afforded 5-aminosulfonyl-3-[(pyrrol-2-yl)(ethylaminocarbonyl)methylene]indolin-2-one; (45 mg), 1H NMR (400 MHz, DMSO-d6) δ 1.16 (t, 3H), 3.36 (q, 2H), 6.40 (s, 1H), 6.64 (s, 1H), 7.02 (d, 1H), 7.20 (brs, 2H), 7.42 (s, 1H), 7.64 (d, 1H), 7.75 (s, 1H), 8.85 (t, 1H), 11.40 (s, 1H) ppm.

Workup

  1. customwas irradiated in a microwave at 160° C. for 5 minutes
  2. washThe resulting mixture was washed with 0.2 N HCl (25 mL) and saturated sodium bicarbonate (25 mL)
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c92f8e153dd342b4abfbe125acf4a83b
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

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