Sodium Iodide → HCID 15549983, compound

HRID 431019Notes

Reaction equation

HRID 431019 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:25][CH2:26][CH2:27]Br)=[C:17]([O:20][CH2:21][CH:22]4[CH2:24][CH2:23]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:29][NH:30][CH:31]1[CH2:35][O:34][C:33](=[O:36])[CH2:32]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:25][CH2:26][CH2:27][N:30]([CH:31]4[CH2:35][O:34][C:33](=[O:36])[CH2:32]4)[CH3:29])=[C:17]([O:20][CH2:21][CH:22]4[CH2:24][CH2:23]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 18762784HCID 18762784, compoundHCID 22270042HCID 22270042, compound

Product 1

HCID 15549983HCID 15549983, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

300 mg of 4-[(3-chloro-4-fluorophenyl)amino]-6-cyclopropylmethoxy-7-(2-bromoethoxy)-quinazoline and 400 mg of 4-methylamino-dihydro-furan-2-one in 20 ml acetonitrile are combined with 240 mg of potassium carbonate and 70 mg of sodium iodide and refluxed for 24 hours. After cooling to ambient temperature the reaction mixture is filtered and the filtrate is evaporated down in vacuo. The flask residue is chromatographed over a silica gel column with methylene chloride/methanol/concentrated aqueous ammonia solution (97:3:0.05) as eluant. The title compound is obtained as a light beige solid.

Workup

  1. temperaturerefluxed for 24 hours
  2. filtrationis filtered
  3. customthe filtrate is evaporated down in vacuo
  4. customThe flask residue is chromatographed over a silica gel column with methylene chloride/methanol/concentrated aqueous ammonia solution (97:3:0.05) as eluant

Sources & evidence

ORD record
ord-37f5eec74edf4881b6e463c306916f45
Source dataset
uspto-grants-2003_12
Patent number
US06656946B2

Reaction notes

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