Triethylamine → HCID 54698276, compound

HRID 458704Notes

Reaction equation

HRID 458704 reaction equation
C([O:9][C:10]1[C:15](=[O:16])[N:14]2[CH2:17][C:18](=[O:23])[NH:19][C:20]([CH3:22])([CH3:21])[C:13]2=[N:12][C:11]=1[C:24]([O:26]CC)=O)(=O)C1C=CC=CC=1.[F:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[F:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH:35][C:24]([C:11]2[N:12]=[C:13]3[C:20]([CH3:21])([CH3:22])[NH:19][C:18](=[O:23])[CH2:17][N:14]3[C:15](=[O:16])[C:10]=2[OH:9])=[O:26])=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 18442525HCID 18442525, compound

Product 1

HCID 54698276HCID 54698276, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Intermediate 30, ethyl 3-(benzoyloxy)-9,9-dimethyl-4,7-dioxo-6,7,8,9-tetrahydro-4H-pyrazino[1,2-a]pyrimidine-2-carboxylate, (1 mmol), was dissolved in 4 mL of DMF. To this was added 4-fluorobenzylamine (0.457 mL, 4 mmol) and triethylamine (0.139 mL, 1 mmol). The mixture was warmed to 80° C. and allowed to stir overnight, after which it was allowed to cool to room temperature and transferred to a seperatory funnel. The mixture was diluted with ethyl acetate, washed with 1N HCl, dried over Na2SO4 then concentrated in vacuo. Methanol and ether were added to the residue and the resulting precipitate isolated by filtration. 1H NMR (500 MHz, DMSO) δ: 1.56 (s, 3H), 4.50 (m, 4H), 7.17 (m, 2H), 7.38 (m, 2H), 8.72 (brs, 1H), 9.37 (brm, 1H), 12.37 (s, 1H).

Workup

  1. temperatureto cool to room temperature
  2. customtransferred to a seperatory funnel
  3. washwashed with 1N HCl
  4. dry with materialdried over Na2SO4
  5. concentrationthen concentrated in vacuo
  6. additionMethanol and ether were added to the residue
  7. customthe resulting precipitate isolated by filtration

Sources & evidence

ORD record
ord-057a8fd781454b83a25935a5ccd33388
Source dataset
uspto-grants-2007_03
Patent number
US07192948B2

Reaction notes

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