Pyrrole-2-carboxaldehyde → HCID 57147096, compound

HRID 2213682Notes

Reaction equation

HRID 2213682 reaction equation
C(O)(=O)C.[NH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10]2.[CH:17]([N:20]([CH:23]([CH3:25])[CH3:24])CC)([CH3:19])C.N1C=CC=C1C=O.N1CCCC1>C(O)C>[NH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[C:10]2=[CH:25][C:23]1[NH:20][CH:17]=[CH:19][CH:24]=1

Participants

6

Reactant 4

HCID 13854Pyrrole-2-carboxaldehydeHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 17982554HCID 17982554, compound

Product 1

HCID 57147096HCID 57147096, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Alternatively, a solution of 5-aminomethylindolin-2-one acetate salt (220 mg, 1 mmol) in ethanol (10 mL) was treated with diisopropylethylamine (DIEA) (3 mL). After 20 minutes, 2-pyrrolecarboxaldehyde (95 mg, 1 mmol) and pyrrolidine (0.05 mL) were added and the reaction mixture was stirred at 60° C. for 3 hours. Concentration of the solvent gave an oil which was purified by reverse phase HPLC (acetonitrile/water) to afford 5-aminomethyl-3-[(pyrrol-2-yl)methylene]indolin-2-one; as a trifluoroacetate salt (70 mg); 1H NMR (400 MHz, DMSO-d6) δ 3.98 (m, 2H), 6.36 (m, 1H), 6.84 (brs, 1H), 6.88 (d, 1H), 7.22 (d, 1H), 7.34 (s, 1H), 7.62 (s, 1H), 7.68 (s, 1H), 8.20 (brs, 2H), 11.00 (s, 1H) ppm.

Workup

  1. customConcentration of the solvent gave an oil which
  2. customwas purified by reverse phase HPLC (acetonitrile/water)

Sources & evidence

ORD record
ord-1968fa71a70549f98c96b784f5c21158
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

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