Ammonia → 2-Aminocarbonylamino-5-(2-naphthyl)pyrrole-3-carboxamide

HRID 416029Notes

Reaction equation

HRID 416029 reaction equation
ClC(Cl)(Cl)[C:3]([N:5]=C=O)=[O:4].[NH2:10][C:11]1[NH:12][C:13]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)=[CH:14][C:15]=1[C:16]([NH2:18])=[O:17].N.CO>O1CCCC1>[NH2:5][C:3]([NH:10][C:11]1[NH:12][C:13]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)=[CH:14][C:15]=1[C:16]([NH2:18])=[O:17])=[O:4]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 76400Trichloroacetyl isocyanateHCID 582940172-Amino-5-(2-naphthyl)pyrrole-3-carboxamide

Product 1

HCID 461809882-Aminocarbonylamino-5-(2-naphthyl)pyrrole-3-carboxamideYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trichloroacetyl isocyanate (470 μL, 4.0 mmol) was added dropwise to a solution of 2-amino-5-(2-naphthyl)pyrrole-3-carboxamide (Reference compound No. 1-1, 1.0 g, 4.0 mmol) in anhydrous tetrahydrofuran (20 mL) at −30° C. over 5 minutes, and the whole was stirred for 1.5 hours. Furthermore, 2.0 M ammonia solution in methanol (20 mL, 40 mmol) was added thereto, and the whole was stirred at room temperature for 3 days. The precipitated solid was filtered off and washed with a mixed solvent of diethylether-ethanol (3:1) (20 mL). The obtained solid was dried at 40° C. under reduced pressure to give the target compound (0.67 g) as a pale gray solid (Yield 58%).

Workup

  1. stirringthe whole was stirred at room temperature for 3 days
  2. filtrationThe precipitated solid was filtered off
  3. washwashed with a mixed solvent of diethylether-ethanol (3:1) (20 mL)
  4. customThe obtained solid was dried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-6678137894a949ada2e36686f4246276
Source dataset
uspto-grants-2012_01
Patent number
US08088817B2

Reaction notes

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