HCID 86634100, compound → HCID 86634101, compound

HRID 2275514Notes

Reaction equation

HRID 2275514 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH:7]=[CH:8][C:9]1[CH:22]=[CH:21][C:20]2[C:11](=[C:12]([NH2:23])[C:13]3[C:18]([N:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][C:9]1[CH:22]=[CH:21][C:20]2[C:11](=[C:12]([NH2:23])[C:13]3[C:18]([N:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86634100HCID 86634100, compound

Product 1

HCID 86634101HCID 86634101, compoundYield 103.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(9-Amino-acridin-2-yl)-acrylic acid tert-butyl ester 6 (40 mg, 0.06 mmol) was dissolved in ethanol (25 mL). 10% Pd/C (15 mg) was added and the solution was put under hydrogenation at 3 bar for 1 h30. The mixture was filtered through Celite and the solvent was evaporated. The residue was purified by Flashmaster II using a gradient elution (DCM→DCM:MeOH 40:60) afforded pure 3-(9-amino-acridin-2-yl)-propionic acid tert-butyl ester 7 as an orange oil (20 mg, 52%). 1H NMR and LCMS analyses conformed to structure.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe solvent was evaporated
  3. customThe residue was purified by Flashmaster II
  4. washa gradient elution (DCM→DCM:MeOH 40:60)

Sources & evidence

ORD record
ord-825c6545e7344e748cc18438945bd968
Source dataset
uspto-grants-2015_09
Patent number
US09127164B2

Reaction notes

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