Potassium Carbonate → Cediranib

HRID 2263483Notes

Reaction equation

[Cl-].[CH2:2]1[N+:5]2([CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:4][CH2:3]1.[F:10][C:11]1[C:19]([O:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([OH:33])=[C:28]([O:31][CH3:32])[CH:29]=3)[N:24]=[CH:23][N:22]=2)=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[C:14]([CH3:34])[NH:15]2.CN1CCCC1=O.C(=O)([O-])[O-].[K+].[K+]>O.C(OC)(C)(C)C>[F:10][C:11]1[C:19]([O:20][C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:33][CH2:4][CH2:3][CH2:2][N:5]4[CH2:9][CH2:8][CH2:7][CH2:6]4)=[C:28]([O:31][CH3:32])[CH:29]=3)[N:24]=[CH:23][N:22]=2)=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[C:14]([CH3:34])[NH:15]2

Participants

Conditions

Temperature: 20 °C

Procedure

4-Azoniaspiro[3,4]octane chloride (1.14 g) was added to a mixture of 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxyquinazolin-7-ol (2.5 g), 1-methyl-2-pyrrolidinone (25 ml), methyl tert-butyl ether (1.8 ml) and potassium carbonate (815 mg) at 80° C. After stirring at 80° C. for 3 hours water (27 ml) was added over 40 minutes. The mixture was allowed to cool to 20° C. and left overnight. The mixture was reheated to 60° C. and filtered. The filter cake was washed with 1:1 v/v 1-methyl-2-pyrrolidinone/water (5 ml) and then with water (4×5 ml). The solid was dried in a vacuum oven to give 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline.

Workup

additionwas added over 40 minutes
customwas reheated to 60° C.
filtrationfiltered
washThe filter cake was washed with 1:1 v/v 1-methyl-2-pyrrolidinone/water (5 ml)
customThe solid was dried in a vacuum oven

Sources & evidence

ORD record: ord-eabc701161824b3ca7ee4c438f99842a
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851623B2

Reaction notes

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