3-Ethylphenyl isocyanate → 2-Acetylamino-4-{4-[3-(3-ethylphenyl)ureido]phenyl}-1H-pyrrole-3-carboxamide

HRID 734651Notes

Reaction equation

HRID 734651 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N:9]=[C:10]=[O:11])[CH:4]=1)[CH3:2].[C:12]([NH:15][C:16]1[NH:17][CH:18]=[C:19]([C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[C:20]=1[C:21]([NH2:23])=[O:22])(=[O:14])[CH3:13]>O1CCCC1>[C:12]([NH:15][C:16]1[NH:17][CH:18]=[C:19]([C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:10]([NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[CH:4]=3)=[O:11])=[CH:26][CH:25]=2)[C:20]=1[C:21]([NH2:23])=[O:22])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 27696373-Ethylphenyl isocyanateHCID 690618602-acetylamino-4-(4-aminophenyl)-1H-pyrrole-3-carboxamide

Product 1

HCID 578455572-Acetylamino-4-{4-[3-(3-ethylphenyl)ureido]phenyl}-1H-pyrrole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.061 cm3 (0.426 mmol) of 1-ethyl-3-isocyanatobenzene is added at room temperature to a suspension of 100 mg (0.387 mmol) of 2-acetylamino-4-(4-aminophenyl)-1H-pyrrole-3-carboxamide in 5 cm3 of anhydrous tetrahydrofuran. The reaction medium is stirred at room temperature for 24 hours and then evaporated to dryness under reduced pressure. The crude product is purified by flash chromatography [eluent; dichloromethane/methanol (97/3 by volume)]. After concentrating under reduced pressure the fractions containing the expected product, 107 mg of 2-acetylamino-4-{4-[3-(3-ethylphenyl)ureido]phenyl}-1H-pyrrole-3-carboxamide are obtained in the form of a brown solid.

Workup

  1. customevaporated to dryness under reduced pressure
  2. customThe crude product is purified by flash chromatography [eluent; dichloromethane/methanol (97/3 by volume)]
  3. concentrationAfter concentrating under reduced pressure the fractions
  4. additioncontaining the expected product, 107 mg of 2-acetylamino-4-{4-[3-(3-ethylphenyl)ureido]phenyl}-1H-pyrrole-3-carboxamide
  5. customare obtained in the form of a brown solid

Sources & evidence

ORD record
ord-d555e076b7cb4949bd1fc8122c71a0aa
Source dataset
uspto-grants-2009_09
Patent number
US07592365B2

Reaction notes

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