Acetic Acid → HCID 66923585, compound

HRID 1364388Notes

Reaction equation

HRID 1364388 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][O:7][C:8]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[C:10]([NH2:19])=[N:11][C:12]([NH2:18])=[N:13]3)=[CH:4][CH:3]=1.[C:22](OC(=O)C)(=[O:24])[CH3:23].[CH3:29][C:30](O)=[O:31]>>[C:22]([NH:18][C:12]1[N:11]=[C:10]([NH:19][C:30](=[O:31])[CH3:29])[C:9]2[C:14](=[CH:15][CH:16]=[CH:17][C:8]=2[O:7][CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:21][CH:20]=2)[N:13]=1)(=[O:24])[CH3:23]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 11573007HCID 11573007, compound

Product 1

HCID 66923585HCID 66923585, compound

Procedure

5-(4-Chlorobenzyloxy)-quinazoline-2,4-diamine (Example 2) (75 mg; 0.25 mmol) is dissolved in 1:1 HOAc: acetic anhydride and heated to 130° C. for 5 hours. After allowing the reaction to room temperature, the solvent is removed under N2 purge. The resulting solid is dissolved in minimal hot ethanol and allowed to cool to room temperature and the resulting crystals are filtered and dried under vacuum overnight to yield 20 milligrams of N-[2-acetylamino-5-(4-chlorobenzyloxy)quinazolin-4-yl]acetamide.

Workup

  1. customthe reaction to room temperature
  2. customthe solvent is removed under N2
  3. custompurge
  4. dissolutionThe resulting solid is dissolved in minimal hot ethanol
  5. filtrationthe resulting crystals are filtered
  6. customdried under vacuum overnight

Sources & evidence

ORD record
ord-66d1848fc2c143d0afe6a3618adf24c2
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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