Ethanol → HCID 17989691, compound

HRID 1271087Notes

Reaction equation

HRID 1271087 reaction equation
[Cl:1][C:2]1[C:3](=[O:29])[N:4]([C:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=4)[N:16]=3)[CH:12]=[CH:11][N:10]=2)[N:5]=[CH:6][C:7]=1Cl.C(=O)([O-])[O-].[K+].[K+].O.[CH2:37]([OH:39])[CH3:38]>>[Cl:1][C:2]1[C:3](=[O:29])[N:4]([C:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=4)[N:16]=3)[CH:12]=[CH:11][N:10]=2)[N:5]=[CH:6][C:7]=1[O:39][CH2:37][CH3:38]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 11430Potassium CarbonateHCID 17989685HCID 17989685, compound

Product 1

HCID 17989691HCID 17989691, compoundYield 35%

Procedure

To a suspension of 4,5-Dichloro-2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-2H-pyridazin-3-one (0.3 g) in ethanol (10 mL) was added of 0.220 mg of potassium carbonate. The mixture was heated to reflux for 4 h. The suspension was poured into water (50 mL) and extracted with ethyl acetate (2×100 mL). The organic phase were combined, dried over MgSO4, and concentrated. Flash silica chromatography, eluting with ethyl acetate-hexane (9:1), afforded the title compound as a solid (0.130 g, 35%). Mp 196–198° C., 1H NMR (CDCl3) 8.80 (1H, d, 3 Hz), 8.60 (1H, d, 6 (1H, s), 8.02 (2H, d, m), 7.93 (1H, s), 7.46 (1H, dd, 6 Hz, 3 Hz), 7.31 (1H,m), 7.29 (1H, d 3 Hz), 7.28 (1H, s), 4.43 (2H, q, 6 Hz), 1.56 (3H, t, 6 Hz).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 h
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. washFlash silica chromatography, eluting with ethyl acetate-hexane (9:1)

Sources & evidence

ORD record
ord-5771399f6a3a47399cfcfb24064b80f6
Source dataset
uspto-grants-2007_04
Patent number
US07205301B2

Reaction notes

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