Pyrrolidine → HCID 22030771, compound

HRID 1791667Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 7-(2,3-epoxypropoxy)-6-methoxy-4-(2-methylindol-5-yloxy) quinazoline (100 mg, 0.27 mmol), (prepared as described for the starting material in Example 162), and pyrrolidine (67 ul, 0.8 mmol) in DMF (4 ml) was heated at 70° C. for 24 hours. The solvent was removed by evaporation and the residue purified by silica column chromatography eluting with dichloromethane/methanol/0.880 aqueous ammonia (100/8/1). The relevant fractions were evaporated to dryness then the residue treated with a little dichloromethane and dried under high vacuum to give 7-(2-hydroxy-3-pyrrolidin-1-ylpropoxy)-6-methoxy-4-(2-methylindol-5-yloxy)quinazoline (44 mg, 37%) as a white foam.

Workup

custom(prepared
customThe solvent was removed by evaporation
customthe residue purified by silica column chromatography
washeluting with dichloromethane/methanol/0.880 aqueous ammonia (100/8/1)
customThe relevant fractions were evaporated to dryness
additionthe residue treated with a little dichloromethane
customdried under high vacuum

Sources & evidence

ORD record: ord-ed7e7184230d4f159c3035aff7748ca7
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074800B1

Reaction notes

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