Acetyl chloride → HCID 68433357, compound

HRID 1162838Notes

Reaction equation

HRID 1162838 reaction equation
C(N(CC)CC)C.F[C:9](F)(F)[C:10]([OH:12])=[O:11].[CH2:15]([N:22]([CH3:50])[CH2:23][CH2:24][CH:25]1[N:30]2[C:31](=[O:40])[N:32]([CH:37]([CH3:39])[CH3:38])[C:33](=[O:36])[C:34](O)=[C:29]2[C:28](=[O:41])[N:27]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=2)[CH2:26]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(Cl)(=O)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:10]([O:12][C:34]1[C:33](=[O:36])[N:32]([CH:37]([CH3:38])[CH3:39])[C:31](=[O:40])[N:30]2[CH:25]([CH2:24][CH2:23][N:22]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:50])[CH2:26][N:27]([CH2:42][C:43]3[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=3)[C:28](=[O:41])[C:29]=12)(=[O:11])[CH3:9]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 68430630HCID 68430630, compound

Product 1

HCID 68433357HCID 68433357, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (370 μL, 2.64 mmol) and DMAP (21 mg, 0.18 mmol) were added to a stirred solution of 4-{2-[benzyl(methyl)amino]ethyl}-2-(4-fluorobenzyl)-9-hydroxy-7-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione trifluoroacetate (from Example 52, 535 mg, 0.88 mmol) in anhydrous CH2Cl2 (10 mL) at 0 C. Acetyl chloride (94 μL, 1.32 mmol) was added and the mixture was then stirred at room temperature for 20 min. The solvent was removed in vacuo and the residue partitioned between EtOAc and saturated aqueous NaHCO3. The layers were separated and the aqueous layer extracted with EtOAc. The combined organic layers were washed successively with water and brine, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as an orange solid which was carried directly into the hydrogenation step. ES MS (M+1)=537.6.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between EtOAc and saturated aqueous NaHCO3
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with EtOAc
  5. washThe combined organic layers were washed successively with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-feded82c6f7c4d67b8b866d980d8254b
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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