Water → HCID 57444136, compound

HRID 1455120Notes

Reaction equation

HRID 1455120 reaction equation
C[N:2]([CH3:5])C=O.[Cl:6][C:7]1[CH:8]=C([CH:12]=[CH:13][C:14]=1N)OC.I[C:17]1[N:26]=[CH:25][C:24]2[CH2:23][CH2:22][C:21]3[C:27]([C:31]([NH2:33])=[O:32])=[N:28][N:29]([CH3:30])[C:20]=3[C:19]=2[N:18]=1.[C:34]([O-])([O-])=O.[K+].[K+].[OH2:40]>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:34][O:40][C:14]1[CH:13]=[CH:12][C:5]([NH:2][C:17]2[N:26]=[CH:25][C:24]3[CH2:23][CH2:22][C:21]4[C:27]([C:31]([NH2:33])=[O:32])=[N:28][N:29]([CH3:30])[C:20]=4[C:19]=3[N:18]=2)=[CH:8][C:7]=1[Cl:6]

Participants

7

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 11430Potassium CarbonateHCID 4074322-Chloro-4-methoxyanilineHCID 442356528-iodo-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

Product 1

HCID 57444136HCID 57444136, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
120 °C

Procedure

Pd(OAc)2 (20 mg, 0.09 mmol, 10%), (±)-BINAP (55 mg, 0.09 mmol, 10%) and dimethylformamide (15 mL) were charged in a round-bottom flask flushed with argon. The mixture was stirred under argon for 30 minutes. Then 3-chloro-p-anisidine (153 mg, 0.97 mmol), 8-iodo-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (300 mg, 0.84 mmol), K2CO3 (2.45 g, 17.8 mmol) and dimethylformamide (6 mL) were added. The resulting mixture was stirred at room temperature for 1 hour and then heated to 120° C. in an oil bath under argon with good stirring for 18 hours. After cooling to room temperature, the reaction mixture was poured into water (300 mL) and extracted with dichloromethane (5×60 mL). The organic extracts were washed with water (2×20 mL) and dried over anhydrous Na2SO4. The solvent was removed under vacuum, the crude solid was taken up with diethyl ether, filtered, washed with diethyl ether and purified by flash chromatography on silica gel (eluant: dichloromethane/methanol 97.5:2.5) to afford 95 mg of pure title compound.

Workup

  1. customflushed with argon
  2. stirringThe resulting mixture was stirred at room temperature for 1 hour
  3. stirringwith good stirring for 18 hours
  4. temperatureAfter cooling to room temperature
  5. extractionextracted with dichloromethane (5×60 mL)
  6. washThe organic extracts were washed with water (2×20 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe solvent was removed under vacuum
  9. filtrationfiltered
  10. washwashed with diethyl ether
  11. custompurified by flash chromatography on silica gel (eluant: dichloromethane/methanol 97.5:2.5)

Sources & evidence

ORD record
ord-d1e787615b4649f29e67d24448722bb9
Source dataset
uspto-grants-2009_01
Patent number
US07482354B2

Reaction notes

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