Triethylamine → HCID 86634100, compound

HRID 2275513Notes

Reaction equation

HRID 2275513 reaction equation
N[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([NH2:16])[C:6]3[C:11]([N:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[C:17]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])[CH:18]=[CH2:19].C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[C:22]([O:21][C:17](=[O:20])[CH:18]=[CH:19][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([NH2:16])[C:6]3[C:11]([N:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 31624Acridine, 2,9-diamino-

Product 1

HCID 86634100HCID 86634100, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

To a 10 mL rbf equipped with a nitrogen bubbler were charged 3-bromo-9-aminoacridine 5 (120 mg, 0.44 mmol), tert-butyl acrylate (75 μL, 0.48 mmol) and anhydrous DMF (1 mL). Tri-(O-tolyl)phosphine (25 mg, 0.08 mmol) and palladium (II) acetate (6 mg, 0.03 mmol) were added. The reaction mixture was stirred at room temperature and degassed by applying nitrogen flow and vacuum successively (3 times). The mixture was finally placed under nitrogen atmosphere and triethylamine (185 μL, 1.32 mmol) was added. The red-orange solution was heated to 110° C. for 3 hours and then cooled to room temperature. The brown-orange solution was filtered through Celite and washed with ethyl acetate. This organic layer was then washed with water and concentrated in vacuo to give the crude product as an orange oil. Purification by Flashmaster II using a gradient elution (DCM→DCM:MeOH 60:40) afforded pure 3-(9-amino-acridin-2-yl)-acrylic acid tert-butyl ester 6 as an orange solid (75 mg, 53%). 1H NMR and LCMS analyses conformed to structure.

Workup

  1. customTo a 10 mL rbf equipped with a nitrogen bubbler
  2. customdegassed
  3. temperatureThe red-orange solution was heated to 110° C. for 3 hours
  4. temperaturecooled to room temperature
  5. filtrationThe brown-orange solution was filtered through Celite
  6. washwashed with ethyl acetate
  7. washThis organic layer was then washed with water
  8. concentrationconcentrated in vacuo
  9. customto give the crude product as an orange oil
  10. customPurification by Flashmaster II
  11. washa gradient elution (DCM→DCM:MeOH 60:40)

Sources & evidence

ORD record
ord-13bb3b038d964442b40cb8e9fa60c18a
Source dataset
uspto-grants-2015_09
Patent number
US09127164B2

Reaction notes

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