Water → 1-(7,8-Bis(4-chlorophenyl)-2-ethyl-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-c]pyrimidin-5-yl)-3-(ethylamino)azetidine-3-carboxamide

HRID 271429Notes

Reaction equation

HRID 271429 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([N:14]3[CH2:17][C:16]([NH:21][CH2:22][CH3:23])([C:18]([NH2:20])=[O:19])[CH2:15]3)[N:11]3[C:24](=[O:27])[NH:25][N:26]=[C:10]3[C:9]=2[C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:42][CH3:43].O>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([N:14]3[CH2:17][C:16]([NH:21][CH2:22][CH3:23])([C:18]([NH2:20])=[O:19])[CH2:15]3)[N:11]3[C:24](=[O:27])[N:25]([CH2:42][CH3:43])[N:26]=[C:10]3[C:9]=2[C:28]2[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 587728451-(7,8-Bis(4-chlorophenyl)-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-c]pyrimidin-5-yl)-3-(ethylamino)azetidine-3-carboxamide

Product 1

HCID 159530981-(7,8-Bis(4-chlorophenyl)-2-ethyl-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-c]pyrimidin-5-yl)-3-(ethylamino)azetidine-3-carboxamideYield 81.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(7,8-bis(4-chlorophenyl)-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-c]pyrimidin-5-yl)-3-(ethylamino)azetidine-3-carboxamide (25 mg, 0.05 mmol) in DMF (0.5 mL) at room temperature under argon was added K2CO3 (10 mg, 0.07 mmol), followed by iodoethane (10 mg, 0.064 mmol). The reaction mixture was stirred at 60° C. in a pre-heated oil bath for 30 min. After the reaction mixture was cooled to room temperature, water (5 mL) and EtOAc (5 mL) were added. The layers were separated. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product thus obtained was purified by preparative reverse phase HPLC (without TFA) to obtain 21.5 mg of the title compound as a white solid. HPLC/MS: retention time=3.465 min, [M+H]30 =526.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customThe layers were separated
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product thus obtained
  7. customwas purified by preparative reverse phase HPLC (without TFA)

Sources & evidence

ORD record
ord-e71ffa1af4dc4650b09277361642f10f
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

Loading…