Sodium Iodide → HCID 67025160, compound

HRID 488419Notes

Reaction equation

HRID 488419 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:13][CH2:14]Cl)(=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9].[Br:16][C:17]1[CH:18]=[C:19]([NH:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([NH:34][C:35]([CH:37]=[CH:38][C:39]([OH:41])=[O:40])=[O:36])[CH:32]=3)[N:27]=[CH:26][N:25]=2)[CH:20]=[CH:21][CH:22]=1.[I-].[Na+]>CS(C)=O.O>[Br:16][C:17]1[CH:18]=[C:19]([NH:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([NH:34][C:35](=[O:36])[CH:37]=[CH:38][C:39]([O:41][CH2:14][O:13][C:7]([C:8]([CH3:11])([CH3:10])[CH3:9])=[O:12])=[O:40])[CH:32]=3)[N:27]=[CH:26][N:25]=2)[CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 87885Chloromethyl pivalateHCID 53786874HCID 53786874, compound

Product 1

HCID 67025160HCID 67025160, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

207 mg of potassium carbonate and 0.144 ml of chloromethyl pivalate are added to 200 mg of 4-[(3-bromophenyl)amino]-6{[(2-carboxy-vinyl)carbonyl]amino}-quinazoline in 2 ml of dimethylsulphoxide. Then a further 30 mg of sodium iodide are added and the reaction mixture is stirred for 48 hours at ambient temperature. For working up, the reaction mixture is diluted with 20 ml of water and extracted with ethyl acetate. The combined extracts are washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated by evaporation. The crude product mixture is purified by chromatography on a silica gel column with methylene chloride/methanol (20:1). Yield: 10 mg (4% of theoryl), Rf value: 0.42 (silica gel, methylene chloride/methanol=9:1) Mass spectrum (EI): m/z=526 [M]*

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts are washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated by evaporation
  5. customThe crude product mixture is purified by chromatography on a silica gel column with methylene chloride/methanol (20:1)

Sources & evidence

ORD record
ord-6ff4b1e57e7b43fda4db37b2401ef129
Source dataset
uspto-grants-2005_12
Patent number
US06972288B1

Reaction notes

Loading…