Triethylamine → HCID 59699661, compound

HRID 901292Notes

Reaction equation

HRID 901292 reaction equation
C(N(CC)CC)C.[CH2:8]([N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][N:23]=2)[C:18](O)=[C:17]([S:26]([CH3:29])(=[O:28])=[O:27])[C:16]1=[O:30])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O=P(Cl)(Cl)[Cl:33]>>[CH2:8]([N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][N:23]=2)[C:18]([Cl:33])=[C:17]([S:26]([CH3:29])(=[O:28])=[O:27])[C:16]1=[O:30])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 59699592HCID 59699592, compound

Product 1

HCID 59699661HCID 59699661, compound

Conditions

Temperature
90 °C

Procedure

Triethylamine (1.2 mL, 8.6 mmol) was added to a suspension of 1-benzyl-4-hydroxy-3-(methylsulfonyl)-[1,8]-naphthyridin-2(1H)-one (114) (0.94 g, 2.9 mmol) in neat POCl3 and heated at 90° C. for 3 h. The solution was cooled and the excess POCl3 was distilled under vacuum. The residue was suspended in water, neutralized by solid NaHCO3, and extracted by dichloromethane. The organic layer was subsequently washed by saturated NaHCO3 solution, water and brine, dried over Na2SO4, and evaporated to yield 1-benzyl-4-chloro-3-(methylsulfonyl)-[1,8]-naphthyridin-2(1H)-one (115) as yellow solid. Yield 0.92 g (92%), mp 191° C. 1H-NMR (DMSO-d6): δ 3.50 (s, 3H), 5.65 (s, 2H), 7.28 (m, 5H), 7.55 (m, 1H), 8.70 (dd, J=1.6, 8.4 Hz, 1H), 8.84 (dd, J=1.6, 4.4 Hz, 1H); EIMS m/z 349 (M+1).

Workup

  1. temperatureThe solution was cooled
  2. distillationthe excess POCl3 was distilled under vacuum
  3. extractionextracted by dichloromethane
  4. washThe organic layer was subsequently washed by saturated NaHCO3 solution, water and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-130a248aa3944a16b8d1889dfa2229e5
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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