Triethylamine → HCID 11372409, compound

HRID 2358254Notes

Reaction equation

HRID 2358254 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[NH2:6][CH2:7][C:8]1[N:12]([CH2:13][N:14]2[CH2:18][CH:17]([C:19]3[CH:24]=[C:23]([F:25])[C:22]([F:26])=[C:21]([F:27])[CH:20]=3)[CH2:16][C:15]2=[O:28])[CH:11]=[N:10][CH:9]=1.CCN(CC)CC>C(Cl)Cl>[O:28]=[C:15]1[CH2:16][CH:17]([C:19]2[CH:24]=[C:23]([F:25])[C:22]([F:26])=[C:21]([F:27])[CH:20]=2)[CH2:18][N:14]1[CH2:13][N:12]1[C:8]([CH2:7][NH:6][C:1](=[O:4])[CH2:2][CH3:3])=[CH:9][N:10]=[CH:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 58911277HCID 58911277, compound

Product 1

HCID 11372409HCID 11372409, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a three necked flask, under argon, propionyl chloride (0.0134 ml) is added to a solution of 1-(5-aminomethyl-imidazol-1-ylmethyl)-4-(3,4,5-trifluoro-phenyl)-pyrrolidin-2-one a34 (0.050 g, 0.15 mmol) and Et3N (0.29 ml) in CH2Cl2 (3 ml) at 0° C. After 1 h, the reaction mixture is quenched with ice-water, extracted with CH2Cl2, dried over MgSO4, filtered and evaporated in vacuo. The crude reaction mixture is purified by chromatography on reverse phase silicagel to afford N-[(1-{[2 oxo-4-(3,4,5-trifluorophenyl)pyrrolidin-1-yl]methyl}-1H-imidazol-5-yl)methyl]propanamide 86(37.2 mg).

Workup

  1. customthe reaction mixture is quenched with ice-water
  2. extractionextracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude reaction mixture
  7. customis purified by chromatography on reverse phase silicagel

Sources & evidence

ORD record
ord-4f8387f03526449f88235b142badd3a2
Source dataset
uspto-grants-2010_07
Patent number
US07763644B2

Reaction notes

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