Potassium Carbonate → HCID 17942741, compound

HRID 855721Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (150 mg, 0.44 mol), (prepared as described for the starting material in Example 2), and 3-(3-furyl)-4,5-dihydro-1H-pyrazol-5-one (80 mg, 0.53 mol) in DMF (2 ml) containing potassium carbonate (92 mg, 0.67 mol) was heated at 100° C. for 2.5 hours. After cooling, the mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4) and evaporated. The residue was purified by chromatography eluting with ethyl acetate/methylene chloride (1/1) followed by methanol/ethyl acetate/methylene chloride (1/4/5), followed by methanol/methylene chloride (1/9) to give 4-(5-(3-furyl)pyrazol-3-yloxy)-6-methoxy-7-(3-morpholinopropoxy)quinazoline hydrochloride (155 mg, 77%).

Workup

custom(prepared
temperatureAfter cooling
customthe mixture was partitioned between ethyl acetate and water
washThe organic layer was washed with brine
dry with materialdried (MgSO4)
customevaporated
customThe residue was purified by chromatography
washeluting with ethyl acetate/methylene chloride (1/1)

Sources & evidence

ORD record: ord-12f427ee47324d79971a17cede375f74
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262201B1

Reaction notes

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