Sodium Iodide → HCID 15547169, compound

HRID 1167172Notes

Reaction equation

HRID 1167172 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[Cl:9][C:10]1[CH:11]=[C:12]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:34][CH2:35][CH2:36][N:37]4[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]4)=[C:25]([O:28][CH:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH:13]=[CH:14][C:15]=1[F:16].CS(O[CH2:48][C@@H:49]1[O:53][C:52](=[O:54])[CH2:51][CH2:50]1)(=O)=O>C(#N)C>[Cl:9][C:10]1[CH:11]=[C:12]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:34][CH2:35][CH2:36][N:37]4[CH2:38][CH2:39][N:40]([CH2:48][C@@H:49]5[O:53][C:52](=[O:54])[CH2:51][CH2:50]5)[CH2:41][CH2:42]4)=[C:25]([O:28][CH:29]4[CH2:30][CH2:31][CH2:32][CH2:33]4)[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH:13]=[CH:14][C:15]=1[F:16]

Participants

6

Reactant 4

HCID 5238Sodium Iodide2×HCID 11430Potassium Carbonate2×HCID 13594221HCID 13594221, compound3×HCID 15547164HCID 15547164, compound

Product 1

HCID 15547169HCID 15547169, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

160 mg of potassium carbonate and 50 mg of sodium iodide are added to 300 mg of 4-[(3-chloro-4-fluorophenyl)amino]-6-cyclopentyloxy-7-[2-(piperazin-1-yl)-ethoxy]-quinazoline in 20 ml of acetonitrile. Then 170 mg of (R)-5-[(methanesulphonyl-oxy)methyl]-2-oxo-tetrahydrofuran are added. The reaction mixture is refluxed for four hours, then a further 0.10 g of (R)-5-[(methanesulphonyloxy)methyl]-2-oxo-tetrahydrofuran are added. After another ten hours of refluxing a further 0.12 g of (R)-5-[(methanesulphonyloxy)methyl]-2-oxo-tetrahydrofuran as well as 0.20 g of potassium carbonate and 70 mg of sodium iodide are added. The reaction mixture is refluxed for another five hours and then left to stand over a weekend. For working up the reaction mixture is filtered and the filtrate is concentrated by evaporation. The crude product is purified by chromatography over a silica gel column with methylene chloride/methanol/concentrated aqueous ammonia solution (95:5:0.05, later 93:7:0.1) as eluant. The title compound is obtained as a white solid.

Workup

  1. temperatureThe reaction mixture is refluxed for four hours
  2. additionare added
  3. temperatureThe reaction mixture is refluxed for another five hours
  4. waitleft
  5. waitto stand over a weekend
  6. filtrationis filtered
  7. concentrationthe filtrate is concentrated by evaporation
  8. customThe crude product is purified by chromatography over a silica gel column with methylene chloride/methanol/concentrated aqueous ammonia solution (95:5:0.05, later 93:7:0.1) as eluant

Sources & evidence

ORD record
ord-096a244b5d2e46d182524bd7ee7efcd0
Source dataset
uspto-grants-2003_09
Patent number
US06617329B2

Reaction notes

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