Acetic Anhydride → HCID 44229607, compound

HRID 927328Notes

Reaction equation

HRID 927328 reaction equation
[O:1]=[C:2]1[N:11]([CH2:12][CH2:13][CH2:14][NH:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:33])[C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)[C:10](=[O:34])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>N1C=CC=CC=1>[C:35]([N:20]([CH2:19][CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13][CH2:12][N:11]1[C:10](=[O:34])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]1=[O:1])[CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:33])[C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)(=[O:37])[CH3:36]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 44229456HCID 44229456, compound

Product 1

HCID 44229607HCID 44229607, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-(3-{4-[3 (2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)propylamino]butylamino}propyl)-4-hydroxybenzamide (1.27 g, 2.72 mmol) was dissolved in 10 mL pyridine and acetic anhydride (0.4 mL, 4.07 mmol) was added thereto. After 2 hours, pyridine was removed by distillation under reduced pressure and dichloromethane and water were added thereto. The organic layer was separated and removed. After concentration under reduced pressure, the remaining residue was treated by silica gel column-chromatography and ion exchange resin to give the title compound of oil form (0.06 g, 4.3%).

Workup

  1. custompyridine was removed by distillation under reduced pressure and dichloromethane and water
  2. additionwere added
  3. customThe organic layer was separated
  4. customremoved
  5. concentrationAfter concentration under reduced pressure
  6. additionthe remaining residue was treated by silica gel column-chromatography and ion exchange resin

Sources & evidence

ORD record
ord-b9b4b95d344543628222fca67469908e
Source dataset
uspto-grants-2016_03
Patent number
US09290480B2

Reaction notes

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