Potassium Carbonate → HCID 25016593, compound

HRID 1878753Notes

Reaction equation

HRID 1878753 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:18][C:19]1[CH:24]=[C:23](F)[CH:22]=[CH:21][N:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:18][C:19]1[CH:24]=[C:23]([N:2]([CH3:1])[CH2:3][CH2:4][N:5]2[C:10](=[O:11])[CH:9]=[CH:8][C:7]([C:12]3[S:13][CH:14]=[C:15]([CH3:17])[CH:16]=3)=[N:6]2)[CH:22]=[CH:21][N:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27827922-Chloro-4-fluoropyridineHCID 59843068HCID 59843068, compound

Product 1

HCID 25016593HCID 25016593, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A suspension of 2-(2-(methylamino)ethyl)-6-(4-methylthiophen-2-yl)pyridazin-3(2H)-one (200 mg, 802 μmol), 2-chloro-4-fluoropyridine (116 mg, 882 μmol), and potassium carbonate (222 mg, 1604 μmol) in DMF (1 mL) was heated to 75° C. for 90 min. The reaction mixture was partitioned between CH2Cl2 (50 mL) and 5% NaHCO3 (20 mL). The organic layer was dried over MgSO4 and concentrated to a solid from toluene under reduced pressure. The solid was triturated with toluene and dried under reduced pressure to give a white solid. MS (ESI pos. ion) m/z (MH+): 361. Calc'd exact mass for C17H17ClN4OS: 360. 1H NMR (400 MHz, Chloroform-d) δ ppm 2.28 (s, 3 H) 3.02 (s, 3 H) 3.83 (t, J=6.27 Hz, 2 H) 4.40 (t, J=6.27 Hz, 2 H) 6.40-6.52 (m, 2 H) 6.85 (d, J=9.54 Hz, 1 H) 6.96 (s, 1 H) 7.13 (s, 1 H) 7.46 (d, J=9.54 Hz, 1 H) 7.86 (d, J=6.02 Hz, 1 H). 13C NMR (101 MHz, Chloroform-d) δ ppm 15.74, 37.62, 48.39, 49.09, 105.64, 105.90, 123.48, 128.03, 129.65, 129.74, 138.18, 138.63, 141.27, 149.19, 152.43, 155.53, 159.78.

Workup

  1. customThe reaction mixture was partitioned between CH2Cl2 (50 mL) and 5% NaHCO3 (20 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated to a solid from toluene under reduced pressure
  4. customThe solid was triturated with toluene
  5. customdried under reduced pressure
  6. customto give a white solid

Sources & evidence

ORD record
ord-1f02b655941e4f4c8c5fd2a1692bc67c
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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