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

HRID 1534963

반응식

HRID 1534963 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
40 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-55d9de875ff842689394b33f7f116b73
출처 데이터셋
uspto-grants-1992_02
특허 번호
US05091432

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