Iodoacetamide → 6-Methoxyquinazoline

HRID 916475Notes

Reaction equation

HRID 916475 reaction equation
N1C2C(=CC(O[C:11]3[C:20]4[C:15](=[CH:16][C:17](OCCCN5CCNCC5)=[C:18]([O:21][CH3:22])[CH:19]=4)[N:14]=[CH:13][N:12]=3)=CN=2)C=C1.ICC(N)=O.C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:22][O:21][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][N:12]=[CH:11]2

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 81531DiisopropylethylamineHCID 58960247HCID 58960247, compound

Product 1

HCID 131268876-MethoxyquinazolineYield 193.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(7-azaindol-5-yloxy)-6-methoxy-7-(3-piperazin-1-ylpropoxy)quinazoline (87 mg, 0.2 mmol), (prepared as described for the starting material in Example 34), iodoacetamide (41 mg, 0.22 mmol) and N,N-diisopropylethylamine (26 mg, 0.22 mmol) in acetonitrile (5 ml) was stirred at reflux for 1 hour and allowed to cool to ambient temperature. The crude reaction mixture was loaded onto a silica column and eluted using methylene chloride/methanol (saturated with ammonia) (92/8) solvent. The relevant fractions were combined and evaporated under vacuum to give a residue which was triturated with acetone, filtered and dried to give 4-(7-azaindol-5-yloxy)-7-[3-(4-carbamoylmethyl)piperazin-1-yl)propoxy]-6-methoxyquinazoline (62 mg, 63%).

Workup

  1. custom(prepared
  2. temperatureat reflux for 1 hour
  3. customThe crude reaction mixture
  4. washeluted
  5. customevaporated under vacuum
  6. customto give a residue which
  7. customwas triturated with acetone
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-09ebbc7ff42642cd8b89432265fe4785
Source dataset
uspto-grants-2007_09
Patent number
US07268230B2

Reaction notes

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