Acetic Acid → HCID 66923585, compound

HRID 2176968Notes

Reaction equation

HRID 2176968 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-360630c8d6804bbc9636d5e4aaded13f
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

Loading…