Water → HCID 136403357, compound

HRID 1534955Notes

Reaction equation

HRID 1534955 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.O.[CH3:26][N:27]([CH3:32])[CH2:28][CH:29]([OH:31])[CH3:30]>CC(C)=O>[CH3:26][N:27]([CH3:32])[CH2:28][CH:29]([OH:31])[CH3:30].[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

Participants

5

Reactant 3

HCID 962WaterHCID 37511DimepranolHCID 135409548Leteprinim

Product 1

HCID 136403357HCID 136403357, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

7.34 g (22.42 mmol) of 4-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]benzoic acid (AIT-0082) was placed in a 500 ml round bottom flask equipped with a magnetic stirring bar. 25 ml of water was added and the white slurry was stirred. 18.6 g, 180.3 mmol of 1-(dimethylamino)-2-propanol (AIT-1000) was added to the stirring slurry. The solution rapidly became homogeneous and the reaction was continued for 90 minutes at room temperature. Acetone (350 ml) was then added, and the stirring solution triturated with methanol until a copious white precipitate formed. The product was collected by vacuum filtration and washed with acetone. After drying, 9.45 g (22.0 mmol) of 4-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]benzoic acid compd. with 1-(dimethylamino)-2-propanol (1:1) (AIT-0083) was obtained. Yield: 98%.

Workup

  1. customequipped with a magnetic stirring bar
  2. customthe stirring solution triturated with methanol until a copious white precipitate
  3. customformed
  4. filtrationThe product was collected by vacuum filtration
  5. washwashed with acetone
  6. customAfter drying

Sources & evidence

ORD record
ord-482ae9b4a2fb4d25987f30caf4405056
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

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