4-(2-Aminoethyl)benzenesulfonamide → HCID 136174287, compound

HRID 1534938Notes

Reaction equation

HRID 1534938 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1.[O:14]=[C:15]1[NH:23][CH:22]=[N:21][C:20]2[N:19]([CH2:24][CH2:25][C:26](OCC)=[O:27])[CH:18]=[N:17][C:16]1=2>C(#N)C>[O:14]=[C:15]1[NH:23][CH:22]=[N:21][C:20]2[N:19]([CH2:24][CH2:25][C:26]([NH:1][CH2:2][CH2:3][C:4]3[CH:5]=[CH:6][C:7]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:8][CH:9]=3)=[O:27])[CH:18]=[N:17][C:16]1=2

Participants

4

Reactant 2

HCID 1696824-(2-Aminoethyl)benzenesulfonamideHCID 135794781Ethyl 3-(6-oxo-3,6-dihydro-9H-purin-9-yl)propanoate

Product 1

HCID 136174287HCID 136174287, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

0.500 g (2.50 mmol) of 4-(2-aminoethyl)benzenesulfonamide was placed into a 10 ml round bottom flask. The flask was heated until the solid had melted. The temperature was adjusted to 150° C. and 250 mg (1.06 mmol) of 3-(1.6-dihydro-6-oxo-9H-purin-9-yl)propionic acid, ethyl ester (AIT-0027) was added and the mixture was heated for one hour with stirring. At this time, 10 ml acetonitrile was added and the solid material was broken up with the aid of a spatula while being stirred. Stirring was continued until there were no more lumps (refluxing acetonitrile). The hot acetonitrile solution was quickly filtered by vacuum and the white solid was washed with acetonitrile and then with ether. This yielded 280 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[2-(4-aminosulfonylphenyl)ethyl]propanamide (AIT-0049) as a white solid. Yield: 68%. m.p. 212°-216° C.

Workup

  1. temperatureThe flask was heated until the solid
  2. customwas adjusted to 150° C.
  3. temperaturethe mixture was heated for one hour
  4. stirringwhile being stirred
  5. stirringStirring
  6. filtrationThe hot acetonitrile solution was quickly filtered by vacuum
  7. washthe white solid was washed with acetonitrile

Sources & evidence

ORD record
ord-76b2050fa8504076b18ecbd3f6aea4e3
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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