Diisopropylethylamine → Ethyl (2E)-4-{[(4-acetyl-1H-pyrrol-2-yl)carbonyl]amino}but-2-enoate

HRID 2284454Notes

Reaction equation

HRID 2284454 reaction equation
FC(F)(F)C(O)=O.[NH2:8][CH2:9]/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13].[C:17]([C:20]1[CH:21]=[C:22]([C:25](=[O:30])C(Cl)(Cl)Cl)[NH:23][CH:24]=1)(=[O:19])[CH3:18].C(N(CC)C(C)C)(C)C>ClCCl>[C:17]([C:20]1[CH:21]=[C:22]([C:25]([NH:8][CH2:9]/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:30])[NH:23][CH:24]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27645281-(4-acetyl-1H-pyrrol-2-yl)-2,2,2-trichloroethanoneHCID 72699081ethyl (2E)-4-aminobut-2-enoate trifluoroacetate

Product 1

HCID 86731548Ethyl (2E)-4-{[(4-acetyl-1H-pyrrol-2-yl)carbonyl]amino}but-2-enoateYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl (2E)-4-aminobut-2-enoate trifluoroacetate (2.665 g, 10.963 mmol) was added to a solution of 1-(4-acetyl-1H-pyrrol-2-yl)-2,2,2-trichloroethanone (1.8 g, 7.07 mmol) and N,N-diisopropylethylamine (DIPEA) (5.4 mL, 32 mmol) in dichloromethane (20 mL) and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated under vacuum and the residue purified by flash chromatography (SiO2, hexane-EtOAc 1:1) to obtain the title compound as an off-white solid (1.2 g, 65% yield).

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe residue purified by flash chromatography (SiO2, hexane-EtOAc 1:1)

Sources & evidence

ORD record
ord-79e0f86870b04a31a460a0d086efbe1c
Source dataset
uspto-grants-2015_09
Patent number
US09145418B2

Reaction notes

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