Ethylamine → HCID 58641450, compound

HRID 1394960Notes

Reaction equation

HRID 1394960 reaction equation
[CH:1]1([C@H:4]([O:26][CH2:27][C:28](OCC)=[O:29])[C:5]([N:7]2[CH2:11][C:10]([C:12]3[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=3[F:19])=[CH:9][C@H:8]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:6])[CH2:3][CH2:2]1.[CH2:33]([NH2:35])[CH3:34]>CO>[CH:1]1([C@H:4]([O:26][CH2:27][C:28]([NH:35][CH2:33][CH3:34])=[O:29])[C:5]([N:7]2[CH2:11][C:10]([C:12]3[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=3[F:19])=[CH:9][C@H:8]2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:6])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6341EthylamineHCID 58641285HCID 58641285, compound

Product 1

HCID 58641450HCID 58641450, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl ({(1S)-1-cyclopropyl-2-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-2-oxoethyl}oxy)acetate (40-1, 16 mg, 0.036 mmol) and ethylamine (10 equiv) in methanol (1 mL) was heated in a sealable tube at 75 deg C. for 20 h. The reaction mixture was concentrated, then purified by reverse-phase liquid chromatography (acetonitrile/H2O with 0.1% TFA present) to provide 2-({(1S)-1-cyclopropyl-2-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-2-oxoethyl}oxy)-N-ethylacetamide (40-2) as a light yellow oil. LRMS m/z (M+H) 441.5 found, 441.5 required.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by reverse-phase liquid chromatography (acetonitrile/H2O with 0.1% TFA present)

Sources & evidence

ORD record
ord-56731cc4aab0475e9b0cdc86fc5046f2
Source dataset
uspto-grants-2008_03
Patent number
US07348440B2

Reaction notes

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