Ethanol → HCID 20085685, compound

HRID 1608826Notes

Reaction equation

HRID 1608826 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1)=[O:5].[NH:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]([Cl:25])=[O:24].C(O)C>CO.C(OCC)(=O)C>[ClH:25].[NH:13]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:8][CH2:7][NH:6][C:4](=[O:5])[C:3]1[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=1[NH:1][C:23]([C:19]1[NH:18][CH:22]=[CH:21][CH:20]=1)=[O:24]

Participants

6

Reactant 3

HCID 702EthanolHCID 224558Pyrrole-2-carbonyl chlorideHCID 200855782-Amino-N-[2-(1H-imidazol-2-yl)ethyl]benzamide

Product 1

HCID 20085685HCID 20085685, compoundYield 70.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The titled compound was prepared substantially in accordance with the method detailed in Example 11 using 1.50 g (0.00651 mol) of 2-amino-N-[2-(1H-imidazol-2-yl)-ethyl]benzamide, prepared as in Example 6A, and 1.36 g (0.0105 mol) of pyrrole-2-carboxylic acid chloride with the exception that after reducing the initial reaction solution to dryness the resultant residue was dissolved in methanol. The resulting solution was refluxed for approximately an hour and then reduced to dryness under reduced pressure to provide a solid. This solid was dissolved in an ethyl acetate/aqueous sodium bicarbonate mixture containing a small amount of ethanol. The resultant layers were separated and the organic layer was washed with a saturated sodium chloride solution, with anhydrous sodium sulfate and then reduced to dryness under reduced pressure. The resultant solid was dissolved in methanol containing diethyl ether and hydrochloric acid. After removing the methanol under reduced pressure, the final product was purified by crystallization from an ethanol/ethyl acetate solution, followed by recrystallization from a methanol/ethyl acetate solution, to provide 1.66 g of the desired titled compound (m.p. 237°-239° C.).

Workup

  1. customThe titled compound was prepared substantially in accordance with the method
  2. temperatureThe resulting solution was refluxed for approximately an hour
  3. customto provide a solid
  4. customThe resultant layers were separated
  5. washthe organic layer was washed with a saturated sodium chloride solution, with anhydrous sodium sulfate
  6. dissolutionThe resultant solid was dissolved in methanol
  7. additioncontaining diethyl ether and hydrochloric acid
  8. customAfter removing the methanol under reduced pressure
  9. customthe final product was purified by crystallization from an ethanol/ethyl acetate solution
  10. customfollowed by recrystallization from a methanol/ethyl acetate solution

Sources & evidence

ORD record
ord-ad510c1953414fe192a4282d23e44fd5
Source dataset
uspto-grants-1995_03
Patent number
US05397798

Reaction notes

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