Dimethylformamide → HCID 86621678, compound

HRID 244606Notes

Reaction equation

HRID 244606 reaction equation
[C:1]12([C:9]3[C:18]4[NH:17][CH2:16][CH2:15][CH2:14][C:13]=4[NH:12][C:11](=O)[CH:10]=3)[CH2:8][CH2:7][C:4]([CH:5]=[CH:6]1)=[CH:3][CH2:2]2.CN(C=O)C.S(Cl)([Cl:27])=O>>[Cl:27][C:11]1[N:12]=[C:13]2[C:18](=[C:9]([C:1]34[CH2:8][CH2:7][C:4]([CH:5]=[CH:6]3)=[CH:3][CH2:2]4)[CH:10]=1)[NH:17][CH2:16][CH2:15][CH2:14]2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 66995254HCID 66995254, compound

Product 1

HCID 86621678HCID 86621678, compoundYield 66%

Conditions

Temperature
70 °C

Procedure

To a solution of 1,4-ethano-8-phenyl-1,2,3,4-tetrahydro-1,5-naphthyridin-6-one (435 mg, 1.72 mmol) in 2.5 ml of thionyl chloride was added 100 μL of DMF, and the reaction mixture was heated at 70° C. for 10 h, and concentrated in vacuo. The residue was poured on ice-water and saturated aq. NaHCO3 solution was added to adjust pH to 10-11. The mixture was extracted with EtOAc (2×50 mL), dried over Na2SO4, concentrated and purified by flash chromatography (EtOAc:hexane, 1:4) to give 6-chloro-1,4-ethano-8-phenyl-1,2,3,4-tetrahydro-1,5-naphthyridine (310 mg, 66%) as a white solid; 1H NMR (CDCl3, 300 MHz) 7.58 (m, 2H), 7.43 (m, 3H), 7.29 (s, 1H), 3.35 (s, 1H), 3.18 (m, 2H), 2.63 (m, 2H), 1.99 (m, 2H), 1.73 (m, 2H) ppm; MS (ES) 271.39 (M+H).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was poured on ice-water and saturated aq. NaHCO3 solution
  3. additionwas added
  4. extractionThe mixture was extracted with EtOAc (2×50 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by flash chromatography (EtOAc:hexane, 1:4)

Sources & evidence

ORD record
ord-6cd3e2f23d754a71bdc0c740cf5bf93b
Source dataset
uspto-grants-2014_02
Patent number
US08658669B2

Reaction notes

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