Diethyl Ether → HCID 10193811, compound

HRID 1662931Notes

Reaction equation

HRID 1662931 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]2[N:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:24])[C:4]=2[CH:3]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].C(N(C(C)C)CC)(C)C.CCOCC>N1C=CC=CC=1>[C:25]([NH:1][C:2]1[CH:15]=[CH:14][C:13]2[N:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:24])[C:4]=2[CH:3]=1)(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 66663373HCID 66663373, compound

Product 1

HCID 10193811HCID 10193811, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6-(2-Amino-9-oxo-9H-acridin-10-yl)hexanoic acid (370 mg: 1.14 mmol) was dissolved in anhydrous pyridine (10 ml) and acetic anhydride (100 μl) followed by diisopropylethylamine (350 μl). The mixture was stirred for 3 hours. The solution was evaporated to dryness under vacuum and the gummy residue dissolved in dichloromethane. The solution was washed with 1.0M hydrochloric acid and then brine. The organic phase was dried with anhydrous magnesium sulphate, filtered and the solvent removed by rotary evaporation to leave a sticky solid. Trituration with ether gave a solid which was dried under vacuum to give 360 mg (86%) of 6-(2-acetamido-9-oxo-9H-acridin-10-yl)hexanoic acid.

Workup

  1. customThe solution was evaporated to dryness under vacuum
  2. dissolutionthe gummy residue dissolved in dichloromethane
  3. washThe solution was washed with 1.0M hydrochloric acid
  4. dry with materialThe organic phase was dried with anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent removed by rotary evaporation
  7. customto leave a sticky solid
  8. customwas dried under vacuum

Sources & evidence

ORD record
ord-fa2d4c75bdfb4687aeb3cf8ae015e069
Source dataset
uspto-grants-2011_10
Patent number
US08034558B2

Reaction notes

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