Benzo-1,3-dioxole-5-methylamine → HCID 136023159, compound

HRID 1534947Notes

Reaction equation

HRID 1534947 reaction equation
[CH2:1]([NH2:11])[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.[O:12]=[C:13]1[NH:21][CH:20]=[N:19][C:18]2[N:17]([CH2:22][CH2:23][C:24](OCC)=[O:25])[CH:16]=[N:15][C:14]1=2>C(#N)C>[O:12]=[C:13]1[NH:21][CH:20]=[N:19][C:18]2[N:17]([CH2:22][CH2:23][C:24]([NH:11][CH2:1][C:2]3[CH:10]=[CH:9][C:8]4[O:7][CH2:6][O:5][C:4]=4[CH:3]=3)=[O:25])[CH:16]=[N:15][C:14]1=2

Participants

4

Reactant 2

HCID 75799Benzo-1,3-dioxole-5-methylamineHCID 135794781Ethyl 3-(6-oxo-3,6-dihydro-9H-purin-9-yl)propanoate

Product 1

HCID 136023159HCID 136023159, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
110 °C

Procedure

0.500 g (3.31 mmol) of piperonylamine was placed into a 10 ml round bottom flask with a magnetic stirring bar and heated to 110° C. and 0.250 g (1.06 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propionic acid, ethyl ester (AIT-0027) was added to the stirring amine. The solution was heated for 40 minutes at which time the reaction mixture had solidified. 10 ml of acetonitrile was added to the residue and the solution was stirred for about 20 min. The white precipitate was collected by Buchner vacuum filtration and was washed with acetonitrile and then with ether. This yielded 245 mg of (AIT-0066) as a white solid. Yield: 68%.

Workup

  1. temperatureThe solution was heated for 40 minutes at which time the reaction mixture
  2. filtrationThe white precipitate was collected by Buchner vacuum filtration
  3. washwas washed with acetonitrile

Sources & evidence

ORD record
ord-efba3de5473f41ce9b0aa9b9880f2093
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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