Water → HCID 178439173, compound

HRID 1809969Notes

Reaction equation

HRID 1809969 reaction equation
[CH2:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)[CH2:2][CH3:3].[NH2:13][C:14]1[NH:18][C:17]([CH2:19][C:20]2[O:24][C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:22][CH:21]=2)=[N:16][C:15]=1[C:30](=[O:32])[NH2:31].C(=O)([O-])O.[Na+].O>C1COCC1>[C:30]([C:15]1[N:16]=[C:17]([CH2:19][C:20]2[O:24][C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:22][CH:21]=2)[NH:18][C:14]=1[NH:13][C:8](=[O:9])[C:7]1[CH:11]=[CH:12][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=1)(=[O:32])[NH2:31]

Participants

6

Reactant 4

HCID 962WaterHCID 1042934-Propylbenzoyl chlorideHCID 516892Sodium BicarbonateHCID 178468825HCID 178468825, compound

Product 1

HCID 178439173HCID 178439173, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

4-Propylbenzoyl chloride (2 ml; 11.9 mM) are added dropwise to 3 g (10.8 mM) of ethyl 5-(5-amino-4-carbamoyl-1H-imidazol-2-ylmethyl)furan-2-carboxylate and 1.8 g of sodium hydrogen carbonate (21.6 mM) in 15 ml of THF. The reaction medium is then stirred at 20° C. for 20 hours. After addition of water, a solid precipitate is formed, which is isolated and purified by chromatography on silica, first using a dichloromethane/acetone mixture (90/10) as eluent, and then a dichloromethane/methanol mixture (90/10) to give 2.9 g of ethyl 5-[4-carbamoyl-5-(4-propylbenzoylamino)-1H-imidazol-2-ylmethyl]furan-2-carboxylate in the form of a white solid.

Workup

  1. customa solid precipitate is formed
  2. customwhich is isolated
  3. custompurified by chromatography on silica

Sources & evidence

ORD record
ord-93a0407bb7664ca2ad0d1dca803657e0
Source dataset
uspto-grants-2013_01
Patent number
US08362057B2

Reaction notes

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