Isopropanol → HCID 10216334, compound

HRID 1179134Notes

Reaction equation

HRID 1179134 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([N:14]=[CH:15][C:16]=3[C:17]3[CH:22]=[CH:21][N:20]=[C:19](SC)[N:18]=3)[N:13]=2)=[CH:4][CH:3]=1.OOS([O-])=O.[K+].CC(O)C.[CH3:35][O:36][C:37]1[CH:43]=[CH:42][C:40]([NH2:41])=[CH:39][CH:38]=1>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([N:14]=[CH:15][C:16]=3[C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:41][C:40]4[CH:42]=[CH:43][C:37]([O:36][CH3:35])=[CH:38][CH:39]=4)[N:18]=3)[N:13]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 7732P-AnisidineHCID 17965470HCID 17965470, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 10216334HCID 10216334, compoundYield 339%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
130 °C

Procedure

To a solution of 6-(4-fluorophenyl)-3-[2-(methylthio)pyrimidin-4-yl]pyrazolo[1,5-b]pyridazine (42 mg, 0.124 mmol) in MeOH (2 mL) was added Oxone (77 mg, 0.124 mmol) in water (1 mL). The reaction mixture was stirred for about 2 hours then water (10 mL) was added. The aqueous layer was washed with EtOAc (3×40 mL) and aqueous NaHCO3 (1×20 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo to give a brown solid. This solid was-added to iPrOH (1.0 mL) and 4-methoxyaniline (20 mg, 0.162 mmol) in a sealed tube. The reaction mixture was heated at an oil bath temperature of 130° C. for about 16 hours. The mixture was cooled to RT and the solid collected by filtration to give the title compound as a brown solid (17 mg, 339% b). 1H-NMR (300 MHz, d6-DMSO) δ 9.41 (s, 1H), 9.14 (d, 1H, J=9.1 Hz), 8.88 (s, 1H), 8.41 (d, 1H, J=5.1 Hz), 8.22 (dd, 2H, J=8.5, 5.6 Hz), 8.02 (d, 1H, J=9.3 Hz), 7.62 (d, 2H, J=8.8 Hz), 7.42 (t, 2H, J=8.8 Hz), 7.30 (d, 1H, J=5.2 Hz), 6.94 (d, 2H, J=8.8 Hz), 3.75 (s, 3H); MS (ESI) (M+H)+ 413.

Workup

  1. washThe aqueous layer was washed with EtOAc (3×40 mL) and aqueous NaHCO3 (1×20 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto give a brown solid
  5. temperatureThe mixture was cooled to RT
  6. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-3be869369af54c87a6bf33a0a1937f1f
Source dataset
uspto-grants-2007_10
Patent number
US07279473B2

Reaction notes

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