Sodium Carbonate → HCID 57411801, compound

HRID 2046178Notes

Reaction equation

HRID 2046178 reaction equation
P(Cl)(Cl)(Cl)=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH:18]=[CH:17][N:16]=[C:15]([N:19](O)[C:20](=[NH:29])[CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:14]2=[O:31])=[CH:9][CH:8]=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[F:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH:18]=[CH:17][N:16]3[N:29]=[C:20]([CH2:21][O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:19]=[C:15]3[C:14]2=[O:31])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 86670202HCID 86670202, compound

Product 1

HCID 57411801HCID 57411801, compoundYield 6.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

Phosphorus oxychloride (0.28 mL, 3.0 mmol) was added to a solution of N-[4-(4-fluoro-phenyl)-3-oxo-3,4-dihydro-pyrazin-2-yl]-N-hydroxy-2-phenoxy-acetamidine (0.35 g. 1.51 mmol) in THF (8 mL) at 0° C. The reaction was stirred at 100° C. for 5 minutes under microwave irradiation. The reaction mixture was basified with a saturated solution of Na2CO3. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 1/99 to 10/90). The desired fractions were collected and the solvents evaporated in vacuo and treated with DIPE to yield 7-(4-fluoro-phenyl)-2-phenoxymethyl-7H-[1,2,4]triazolo[1,5-a]pyrazin-8-one (32 mg, 6% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 5.33 (s, 2H), 6.97 (t, J=7.4 Hz, 1H), 7.07 (d, J=7.8 Hz, 2H), 7.26-7.36 (m, 2H), 7.36-7.44 (m, 2H), 7.45 (d, J=6.1 Hz, 1H), 7.50-7.62 (m, 2H), 8.03 (d, J=5.8 Hz, 1H).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo
  5. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 1/99 to 10/90)
  6. customThe desired fractions were collected
  7. customthe solvents evaporated in vacuo
  8. additiontreated with DIPE

Sources & evidence

ORD record
ord-d09a8c0ad5354ee4b66035f1be46d454
Source dataset
uspto-grants-2013_11
Patent number
US08592422B2

Reaction notes

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