8-Chloro-3-methoxy-1,5-naphthyridine → HCID 59843005, compound

HRID 1878750Notes

Reaction equation

HRID 1878750 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][N:5]1[C:10](=[O:11])[CH:9]=[CH:8][C:7]([C:12]2[S:13][CH:14]=[C:15]([CH3:17])[CH:16]=2)=[N:6]1.Cl[C:19]1[CH:20]=[CH:21][N:22]=[C:23]2[C:28]=1[N:27]=[CH:26][C:25]([O:29][CH3:30])=[CH:24]2>CC(O)C>[CH3:30][O:29][C:25]1[CH:24]=[C:23]2[C:28]([C:19]([N:2]([CH3:1])[CH2:3][CH2:4][N:5]3[C:10](=[O:11])[CH:9]=[CH:8][C:7]([C:12]4[S:13][CH:14]=[C:15]([CH3:17])[CH:16]=4)=[N:6]3)=[CH:20][CH:21]=[N:22]2)=[N:27][CH:26]=1

Participants

4

Reactant 2

HCID 594273408-Chloro-3-methoxy-1,5-naphthyridineHCID 59843068HCID 59843068, compound

Product 1

HCID 59843005HCID 59843005, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 2-(2-(methylamino)ethyl)-6-(4-methylthiophen-2-yl)pyridazin-3(2H)-one (275 mg, 1103 μmol) and 8-chloro-3-methoxy-1,5-naphthyridine (193 mg, 993 μmol) in iPrOH (5 mL) was heated to 100° C. for 18 h in an appropriately sealed vial. The mixture was partitioned between CH2Cl2 (30 mL) and 1M NaOH (10 mL), and the organic dried over MgSO4. After concentration under reduced pressure, the organic residue was dissolved in iPrOH (2 mL) and the resulting crystallized solid was washed with iPrOH (2×0.5 mL) then dried under reduced pressure. MS (ESI pos. ion) m/z (MH+): 408. Calc'd exact mass for C21H21N5O2S: 407. 1H NMR (400 MHz, Chloroform-d) δ ppm 2.26 (s, 3 H) 3.22 (s, 3 H) 3.83 (s, 3 H) 4.51 (t, J=5.77 Hz, 2 H) 4.75 (t, J=5.77 Hz, 2 H) 6.55 (d, J=5.52 Hz, 1H) 6.60 (d, J=9.54 Hz, 1 H) 6.91 (s, 1 H) 6.97 (s, 1 H) 7.19 (d, J=9.54 Hz, 1 H) 7.32 (d, J=3.01 Hz, 1 H) 8.32 (d, J=5.52 Hz, 1 H) 8.46 (d, J=2.51 Hz, 1 H).

Workup

  1. customThe mixture was partitioned between CH2Cl2 (30 mL) and 1M NaOH (10 mL)
  2. dry with materialthe organic dried over MgSO4
  3. concentrationAfter concentration under reduced pressure
  4. dissolutionthe organic residue was dissolved in iPrOH (2 mL)
  5. customthe resulting crystallized solid
  6. washwas washed with iPrOH (2×0.5 mL)
  7. customthen dried under reduced pressure

Sources & evidence

ORD record
ord-416f08329f4d45cbb707535b9af5f1f4
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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