Leteprinim → HCID 136140278, compound

HRID 1534956Notes

Reaction equation

HRID 1534956 reaction equation
[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([NH:15][C:16]3[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=3)=[O:14])[CH:5]=[N:4][C:3]1=2>C1C=CC=CC=1>[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([NH:15][C:16]3[CH:24]=[CH:23][C:19]([C:20]([O:22][CH:3]([CH3:2])[CH2:7][N:6]([CH3:11])[CH3:5])=[O:21])=[CH:18][CH:17]=3)=[O:14])[CH:5]=[N:4][C:3]1=2

Participants

3

Reactant 1

HCID 135409548Leteprinim

Product 1

HCID 136140278HCID 136140278, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2.0 g (5.78 mmol) of 4-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]benzoic acid (AIT-0082) were placed into a 100 ml round bottom flask equipped with a magnetic stirring bar, reflux condenser and a drying tube. 16 ml of thionyl/chloride were added and the mixture was slowly heated to 55°-60° C. for six hours. The reaction mixture was allowed to cool to room temperature. 50 ml of benzene were added to break up the crystal mass. The solid was collected by filtration, washed twice with 10 ml of benzene and was allowed to dry under the hood for two hours. While the product was being dried, 20 ml of dimethylamino-2-propanol were placed in a 100 ml round bottom flask equipped with a magnetic stirring bar and drying tube. The mass was slowly added under stirring conditions. The drying tube was replaced on the flask and the stirring continued for six hours at room temperature. The reaction mixture was poured into a 500 ml Erlenmeyer flask containing 300 ml of acetonitrile. The solution was stirred for five minutes. The flask was covered with parafilm and was allowed to stand in the hood overnight at room temperature. The solid material was removed by filtration, washed twice with 15 ml of acetonitrile and air dried under the hood for three hours. The weight of the product 4-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]benzoic acid, 1-(dimethylamino)-2-propyl ester (AIT-0084) was 830 mg. Yield: 33%

Workup

  1. customequipped with a magnetic stirring bar
  2. temperaturereflux condenser and a drying tube
  3. temperaturethe mixture was slowly heated to 55°-60° C. for six hours
  4. filtrationThe solid was collected by filtration
  5. washwashed twice with 10 ml of benzene
  6. customto dry under the hood for two hours
  7. customWhile the product was being dried
  8. custom20 ml of dimethylamino-2-propanol were placed in a 100 ml round bottom flask
  9. customequipped with a magnetic stirring bar
  10. customdrying tube
  11. additionThe mass was slowly added under stirring conditions
  12. additionThe reaction mixture was poured into a 500 ml Erlenmeyer flask
  13. additioncontaining 300 ml of acetonitrile
  14. customto stand in the hood overnight at room temperature
  15. customThe solid material was removed by filtration
  16. washwashed twice with 15 ml of acetonitrile and air
  17. customdried under the hood for three hours

Sources & evidence

ORD record
ord-2418d7d1955e4bd39d158c9dd1e9cb70
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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