Triethylamine → HCID 69545103, compound

HRID 2213677Notes

Reaction equation

HRID 2213677 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]([O:17][C:18]([C:20]([C:22]1[NH:23][CH:24]=[CH:25][CH:26]=1)=O)=[O:19])[CH3:16].C(N(CC)CC)C>C(O)C>[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]([O:17][CH2:15][CH3:16])=[O:19])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 294762ethyl 2-oxo-2-(1H-pyrrol-2-yl)acetateHCID 101982322-Oxoindoline-5-sulfonamide

Product 1

HCID 69545103HCID 69545103, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Alternatively, a mixture of 5-aminosulfonylindolin-2-one (1.0 g, 4.7 mmol), 2-ethoxycarbonylcarbonylpyrrole (2.5 g, 14.5 mmol) in ethanol (120 mL) was treated with triethylamine (1.0 mL, 7.2 mmol). The reaction mixture was refluxed for 24 hours. The reaction mixture was concentrated to approximately 20 mL, treated with additional triethylamine (0.2 mL, 1.44 mmol) and refluxed for 55 hoursr. The reaction was then cooled to ambient temperature and concentrated. Reverse phase HPLC using acetonitrile/water afforded 5-aminosulfonyl-3-[(pyrrol-2-yl)(ethoxycarbonyl)methylene]indolin-2-one; 1H NMR (400 MHz, DMSO-d6) δ 1.35 (t, 3H), 4.50 (q, 2H), 6.40 (s, 1H), 6.65 (s, 1H), 7.06 (d, 1H), 7.25(s, 2H), 7.48 (br s, 1H), 7.50 (s, 1H), 7.68 (d, 1H), 11.50 (s, 1H) ppm; (45 mg) and 5-aminosulfonyl-3-[(pyrrol-2-yl)(carboxy)methylene]indolin-2-one; 1H NMR (400 MHz, DMSO-d6) δ 6.40 (s, 1H), 6.65 (s, 1H), 7.06 (d, 1H), 7.25 (s, 2H), 7.48 (br s, 1H), 7.68 (d, 1H), 7.85 (s, 1H), 11.50 (s, 1H) ppm; (48 mg).

Workup

  1. temperatureThe reaction mixture was refluxed for 24 hours
  2. concentrationThe reaction mixture was concentrated to approximately 20 mL
  3. temperaturerefluxed for 55 hoursr
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-363dd7cd2c9045c1912fafd3fc2cbe96
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

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