Hydrochloric Acid → HCID 68432475, compound

HRID 1162839Notes

Reaction equation

HRID 1162839 reaction equation
[C:1]([O:4][C:5]1[C:10](=[O:11])[N:9]([CH:12]([CH3:14])[CH3:13])[C:8](=[O:15])[N:7]2[CH:16]([CH2:29][CH2:30][N:31](CC3C=CC=CC=3)[CH3:32])[CH2:17][N:18]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:19](=[O:20])[C:6]=12)(=[O:3])[CH3:2].Cl>CO>[C:1]([O:4][C:5]1[C:10](=[O:11])[N:9]([CH:12]([CH3:14])[CH3:13])[C:8](=[O:15])[N:7]2[CH:16]([CH2:29][CH2:30][NH:31][CH3:32])[CH2:17][N:18]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[C:19](=[O:20])[C:6]=12)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68433357HCID 68433357, compound

Product 1

HCID 68432475HCID 68432475, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-{2-[Benzyl(methyl)amino]ethyl}-2-(4-fluorobenzyl)-7-isopropyl-1,6,8-trioxo-1,3,4,6,7,8-hexahydro-2H-pyrazino[1,2-c]pyrimidin-9-yl acetate (456 mg, 0.85 mmol) was suspended in degassed MeOH (10 mL). Aqueous HCl (6 M) was added dropwise until all the solids dissolved. The resulting stirred solution was degassed and purged with nitrogen three times. Palladium on carbon (10%, 131 mg) was added and the mixture was again degassed and purged with nitrogen (×3) and was then placed under hydrogen atmosphere (balloon) and stirred overnight at room temperature. The mixture was filtered through Celite, washing the filter cake well with MeOH. The filtrate was concentrated in vacuo and the residual oil triturated with diethyl ether to afford the hydrochloride salt of the title compound as a bright yellow solid. ES MS (M+1)=447.5.

Workup

  1. dissolutiondissolved
  2. customwas degassed
  3. custompurged with nitrogen three times
  4. additionPalladium on carbon (10%, 131 mg) was added
  5. customthe mixture was again degassed
  6. custompurged with nitrogen (×3)
  7. stirringstirred overnight at room temperature
  8. filtrationThe mixture was filtered through Celite
  9. washwashing the filter cake well with MeOH
  10. concentrationThe filtrate was concentrated in vacuo
  11. customthe residual oil triturated with diethyl ether

Sources & evidence

ORD record
ord-cd1be9ec7f034990b271979574c1fd83
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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