Sodium Iodide → HCID 68699156, compound

HRID 1352220Notes

Reaction equation

HRID 1352220 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[C:9]1([C@H:15]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:31][CH2:32][CH2:33]OS(C)(=O)=O)=[C:25]([N+:28]([O-:30])=[O:29])[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH3:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[NH:39]1[CH2:42][CH2:41][CH2:40]1>C(#N)C.C(Cl)Cl.CO>[C:9]1([C@H:15]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:31][CH2:32][CH2:33][N:39]4[CH2:42][CH2:41][CH2:40]4)=[C:25]([N+:28]([O-:30])=[O:29])[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH3:16])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10422AzetidineHCID 11430Potassium CarbonateHCID 54148143HCID 54148143, compound

Product 1

HCID 68699156HCID 68699156, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
70 °C

Procedure

221 mg of dried potassium carbonate and 50 mg of sodium iodide were given to 600 mg of 4-[(R)-(1-phenylethyl)amino]-7-[2-methanesulfonyloxyethoxy]-6-nitroquinazoline and 0.34 ml of azetidine in 5.0 ml of acetonitrile. The reaction mixture was heated up to 70° C. with stirring. Subsequently 3 ml of acetonitrile were added after one hour and the mixture was stirred for further about 40 hours at 70° C. The solvent was removed in vacuo and the obtained residue was mixed with ice water. The precipitate was suction filtered and dried. The aqueous phase was extracted with methylene chloride and evaporated. The combined precipitates were dissolved in ethyl acetate and stirred together with a little of silica gel and 120 mg of charcoal for further purification. The obtained suspension was filtered and evaporated yielding a yellow resin. Yield: 518 mg (95% of theory); Rf value: 0.40 (silica gel, methylene chloride/methanol/concentrated aqueous ammonia solution 90:10:0.1); mass spectrum (ESI+): m/z=394 [M+H]+.

Workup

  1. stirringthe mixture was stirred for further about 40 hours at 70° C
  2. customThe solvent was removed in vacuo
  3. additionthe obtained residue was mixed with ice water
  4. filtrationfiltered
  5. customdried
  6. extractionThe aqueous phase was extracted with methylene chloride
  7. customevaporated
  8. customThe combined precipitates
  9. dissolutionwere dissolved in ethyl acetate
  10. stirringstirred together with a little of silica gel and 120 mg of charcoal
  11. customfor further purification
  12. filtrationThe obtained suspension was filtered
  13. customevaporated
  14. customyielding a yellow resin

Sources & evidence

ORD record
ord-a16e6e36dcc94ef7a295282def9237c3
Source dataset
uspto-grants-2007_05
Patent number
US07220750B2

Reaction notes

Loading…