Water → 4-(5-(4-Methoxyphenyl)pyrazol-3-yloxy)-6-methoxy-7-(1-(2-methylsulphonylethyl)piperidin-4-ylmethoxy)quinazoline

HRID 855727Notes

Reaction equation

HRID 855727 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH2:18][CH2:17]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH2:40][C:39](=[O:41])[NH:38][N:37]=2)=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:28][O:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]2[NH:37][N:38]=[C:39]([O:41][C:2]3[C:11]4[C:6](=[CH:7][C:8]([O:14][CH2:15][CH:16]5[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH2:18][CH2:17]5)=[C:9]([O:12][CH3:13])[CH:10]=4)[N:5]=[CH:4][N:3]=3)[CH:40]=2)=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6053665-(4-Methoxyphenyl)-2,4-dihydro-3H-pyrazol-3-oneHCID 220305344-Chloro-6-methoxy-7-((1-(2-methylsulphonylethyl)piperidin-4-yl)methoxy)quinazoline

Product 1

HCID 98080604-(5-(4-Methoxyphenyl)pyrazol-3-yloxy)-6-methoxy-7-(1-(2-methylsulphonylethyl)piperidin-4-ylmethoxy)quinazolineYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 4-chloro-6-methoxy-7-(1-(2-methylsulphonylethyl)piperidin-4-ylmethoxy)quinazoline (115 mg, 0.28 mol) and 3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-5-one (65 mg, 0.33 mol), (prepared as described for the starting material in Example 10), in DMF (1.5 ml) containing potassium carbonate (60 mg, 0.42 mol) was heated at 100° C. for 30 minutes. After cooling, water was added. The precipitate was collected by filtration, washed with water and dried under vacuum. The solid was dissolved in methylene chloride/methanol and pentane was added. The precipitate was collected by filtration, washed with pentane and dried under vacuum to give 4-(5-(4-methoxyphenyl)pyrazol-3-yloxy)-6-methoxy-7-(1-(2-methylsulphonylethyl)piperidin-4-ylmethoxy)quinazoline (120 mg, 75%).

Workup

  1. custom(prepared
  2. temperatureAfter cooling
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried under vacuum
  6. dissolutionThe solid was dissolved in methylene chloride/methanol
  7. additionpentane was added
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with pentane
  10. customdried under vacuum

Sources & evidence

ORD record
ord-87f9614976544c85a6b0deec483021b6
Source dataset
uspto-grants-2007_08
Patent number
US07262201B1

Reaction notes

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