Dimethyl Sulfoxide → 4-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]-N-[2-(diethylamino)ethyl]benzamide monohydrochloride

HRID 1534963Notes

Reaction equation

HRID 1534963 reaction equation
[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([O:15]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH:5]=[N:4][C:3]1=2.[CH3:25][CH2:26][N:27]([CH2:30][CH2:31][NH:32][C:33]([C:35]1[CH:36]=[CH:37][C:38]([NH2:41])=[CH:39][CH:40]=1)=[O:34])[CH2:28][CH3:29].[ClH:42].CS(C)=O>CC(C)=O>[ClH:42].[O:1]=[C:2]1[NH:10][CH:9]=[N:8][C:7]2[N:6]([CH2:11][CH2:12][C:13]([NH:41][C:38]3[CH:37]=[CH:36][C:35]([C:33]([NH:32][CH2:31][CH2:30][N:27]([CH2:28][CH3:29])[CH2:26][CH3:25])=[O:34])=[CH:40][CH:39]=3)=[O:15])[CH:5]=[N:4][C:3]1=2

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 66068Procainamide HydrochlorideHCID 1359739573-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester

Product 1

HCID 1364033624-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]-N-[2-(diethylamino)ethyl]benzamide monohydrochloride

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

0.300 g (0.9111 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propanoic acid, 4-nitrophenyl ester (AIT-0081) was placed into a 10 ml round bottom flask with 0.250 g (0.9198 mmol) of procainamide hydrochloride. 2 ml of dimethylsulfoxide was added and the solution was heated to 40° C. for four days. The solution was then poured into 40 ml acetone and was stirred vigorously for 20 minutes. The solid was collected by vacuum filtration and washed with acetone. The solid was placed into a 25 ml round bottom flask with 5 ml ethanol and was stirred for 15 minutes. The solid was collected by vacuum filtration and washed with ethanol and then with ether. This yielded 133 mg of 4-[[3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-1-oxopropyl]amino]-N-[2-(diethylamino)ethyl]-benzamide monohydrochloride (AIT-0095) as a slightly yellow non-hygroscopic solid. m.p. 210°-213° C. (no decomposition).

Workup

  1. filtrationThe solid was collected by vacuum filtration
  2. washwashed with acetone
  3. customThe solid was placed into a 25 ml round bottom flask with 5 ml ethanol
  4. stirringwas stirred for 15 minutes
  5. filtrationThe solid was collected by vacuum filtration
  6. washwashed with ethanol

Sources & evidence

ORD record
ord-55d9de875ff842689394b33f7f116b73
Source dataset
uspto-grants-1992_02
Patent number
US05091432

Reaction notes

Loading…