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Potassium Carbonate → Cediranib

HRID 2263484
Notes
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Reaction equation

HRID 2263484 reaction equation
[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18](O)=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:25])[NH:6]2.[C:26](=[O:29])([O-])[O-].[K+].[K+].[C:32](OC)([CH3:35])([CH3:34])C>CN1CCCC1=O>[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:29][CH2:26][CH2:4][CH2:5][N:6]4[CH2:35][CH2:32][CH2:34][CH2:7]4)=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:25])[NH:6]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15413tert-Butyl methyl etherHCID 1355308324-((4-Fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-ol

Product 1

HCID 9933475Cediranib

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxyquinazolin-7-ol (2.5 g) in 1-methyl-2-pyrrolidinone (25 ml) and methyl tert-butyl ether (1.8 ml) was added potassium carbonate (815 mg). The mixture was degassed by holding under vacuum and letting down with nitrogen. This was carried out five times. The mixture was heated to 80° C. and 4-azoniaspiro[3,4]octane bromide (1.75 g) was added. The mixture was maintained at 80° C. for 3.5 hours. To the hot mixture was added water (27 ml) over 2 hours. The mixture was cooled to 64° C. and the solid filtered. The solid was washed with 1:1 v/v 1-methyl-2-pyrrolidinone/water (5 ml) and then 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

  1. customThe mixture was degassed
  2. addition4-azoniaspiro[3,4]octane bromide (1.75 g) was added
  3. temperatureThe mixture was maintained at 80° C. for 3.5 hours
  4. additionTo the hot mixture was added water (27 ml) over 2 hours
  5. temperatureThe mixture was cooled to 64° C.
  6. filtrationthe solid filtered
  7. washThe solid was washed with 1:1 v/v 1-methyl-2-pyrrolidinone/water (5 ml)
  8. customThe solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-af4bedf7b4a14ab0adc74270cf29356d
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07851623B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes