Perchloric Acid → HCID 59764747, compound

HRID 406513Notes

Reaction equation

HRID 406513 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[CH:7][N:6]=[C:5]2[NH:13][CH2:14][C:15]([N:17]1[CH2:25][CH2:24][C:19]2(OCC[O:20]2)[CH2:18]1)=[O:16].Cl(O)(=O)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[CH:7][N:6]=[C:5]2[NH:13][CH2:14][C:15]([N:17]1[CH2:25][CH2:24][C:19](=[O:20])[CH2:18]1)=[O:16]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 59764852HCID 59764852, compound

Product 1

HCID 59764747HCID 59764747, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring 0° C. solution of 2-(6,7-dichloroquinazolin-4-ylamino)-1-(1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)ethanone (0.603 g, 1.57 mmol) (prepared by general procedures G, F, M) in DCM (15 mL) was slowly added perchloric acid (0.406 mL, 4.72 mmol). The mixture was allowed to warm to room temperature and stirred for about 1 hour. The solvent was decanted and discarded. The remaining solid was washed with aqueous sodium carbonate (10 mL) and water (10 mL) and then dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 1-(2-(6,7-dichloroquinazolin-4-ylamino)acetyl)pyrrolidin-3-one (0.493 g, 1.45 mmol) as white solid which was used in subsequent reactions without further purification. RP-HPLC (Table 1, Method b) Rt 1.62 min; m/z: (M+H)+ 339.

Workup

  1. customTo a stirring 0° C.
  2. customThe solvent was decanted
  3. washThe remaining solid was washed with aqueous sodium carbonate (10 mL) and water (10 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4bf5dca652f140ad89232c8b469b9049
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Reaction notes

Loading…