Pyridine → HCID 59843090, compound

HRID 1878779Notes

Reaction equation

HRID 1878779 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14](=[O:17])[N:13]([CH2:18][CH2:19][O:20][C:21]3[C:30]4[C:25](=[CH:26][C:27]([O:31][CH3:32])=[CH:28][CH:29]=4)[N:24]=[CH:23][CH:22]=3)[N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.N1C=CC=CC=1.S(Cl)(Cl)=O>>[Cl:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14](=[O:17])[N:13]([CH2:18][CH2:19][O:20][C:21]3[C:30]4[C:25](=[CH:26][C:27]([O:31][CH3:32])=[CH:28][CH:29]=4)[N:24]=[CH:23][CH:22]=3)[N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]#[N:6]

Participants

4

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 25016079HCID 25016079, compound

Product 1

HCID 59843090HCID 59843090, compound

Conditions

Temperature
23 °C

Procedure

See example 75 for a general synthesis. To a solution of 2-chloro-4-(1-(2-(7-methoxyquinolin-4-yloxy)ethyl)-6-oxo-1,6-dihydropyridazin-3-yl)benzamide (120 mg, 266 μmol) in pyridine (10763 μL, 133075 μmol) was added thionyl chloride (194 μL, 2661 μmol). The reaction was then stirred overnight at 23° C. for 18 hours. The reaction was then chilled to 0° C., and quenched with sat. NH4Cl. The organic contents were extracted with DCM (30 mL), separated, dried over MgSO4, then concentrated to a solid under reduced pressure. The product was then purified on silica (12 g) eluting with 3>5% of NH3 in MeOH/DCM and isolated as an off white solid. MS (ESI pos. ion) m/z: (MH+); calc'd for C23H17ClN4O3: 432. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.92 (s, 3 H) 4.67 (t, J=5.02 Hz, 2 H) 4.81 (t, J=5.27 Hz, 2 H) 6.65 (d, J=5.52 Hz, 1 H) 6.99 (dd, J=9.29, 2.26 Hz, 1 H) 7.09 (d, J=9.54 Hz, 1 H) 7.30 (s, 1 H) 7.65 (d, J=9.54 Hz, 2 H) 7.68-7.74 (m, 1 H) 7.87 (s, 1 H) 7.95 (d, J=9.54 Hz, 1 H) 8.64 (d, J=5.02 Hz, 1 H).

Workup

  1. customfor a general synthesis
  2. temperatureThe reaction was then chilled to 0° C.
  3. customquenched with sat. NH4Cl
  4. extractionThe organic contents were extracted with DCM (30 mL)
  5. customseparated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to a solid under reduced pressure
  8. customThe product was then purified on silica (12 g)
  9. washeluting with 3>5% of NH3 in MeOH/DCM
  10. customisolated as an off white solid

Sources & evidence

ORD record
ord-dfb06f72953a4e44976e5ef6fb0e8cfa
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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