N,N-Dimethyl-1,3-propanediamine → 2,2'-(Disulphanediyldiethane-2,1-diyl)bis[6-{[3-(dimethylamino)propyl]-amino}-1H-benzo[de]isoquinoline-1,3(2H)-dione]

HRID 1043352Notes

Reaction equation

HRID 1043352 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:38])[N:7]([CH2:16][CH2:17][S:18][S:19][CH2:20][CH2:21][N:22]3[C:31](=[O:32])[C:30]4[CH:33]=[CH:34][C:35](Cl)=[C:28]5[C:29]=4[C:24](=[CH:25][CH:26]=[CH:27]5)[C:23]3=[O:37])[C:8](=[O:15])[C:9]3[C:14]=2[C:13]=1[CH:12]=[CH:11][CH:10]=3.[CH3:39][N:40]([CH3:45])[CH2:41][CH2:42][CH2:43][NH2:44]>>[S:19]([CH2:20][CH2:21][N:22]1[C:31](=[O:32])[C:30]2[CH:33]=[CH:34][C:35]([NH:44][CH2:43][CH2:42][CH2:41][N:40]([CH3:45])[CH3:39])=[C:28]3[C:29]=2[C:24](=[CH:25][CH:26]=[CH:27]3)[C:23]1=[O:37])[S:18][CH2:17][CH2:16][N:7]1[C:6](=[O:38])[C:5]2[CH:4]=[CH:3][C:2]([NH:44][CH2:43][CH2:42][CH2:41][N:40]([CH3:45])[CH3:39])=[C:13]3[C:14]=2[C:9](=[CH:10][CH:11]=[CH:12]3)[C:8]1=[O:15]

Participants

3

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 594288842,2'-(Disulphanediyldiethane-2,1-diyl)bis(6-chloro-1H-benzo[de]-isoquinoline-1,3(2H)-dione)

Product 1

HCID 594288912,2'-(Disulphanediyldiethane-2,1-diyl)bis[6-{[3-(dimethylamino)propyl]-amino}-1H-benzo[de]isoquinoline-1,3(2H)-dione]

Conditions

Temperature
110 °C

Procedure

4 g of (6-chloro-2-(2-{[2-(6-chloro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)ethyl]-disulphanyl}ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione are suspended in 40 ml of N,N-dimethylpropane-1,3-diamine. The mixture is heated with stirring at 110° C. for 12 hours. After cooling, a yellow precipitate is collected, and 500 ml of a 1/1 ethanol/water mixture are added dropwise to the filtrate. The yellow paste obtained is isolated and triturated with 200 ml of acetone. The solids obtained are washed with 300 ml of water and dried. 4.5 g of yellow powder are recovered. The analyses show that the product is in accordance with the expected product.

Workup

  1. temperatureThe mixture is heated
  2. temperatureAfter cooling
  3. customa yellow precipitate is collected
  4. addition500 ml of a 1/1 ethanol/water mixture are added dropwise to the filtrate
  5. customThe yellow paste obtained
  6. customis isolated
  7. customtriturated with 200 ml of acetone
  8. customThe solids obtained
  9. washare washed with 300 ml of water
  10. customdried
  11. custom4.5 g of yellow powder are recovered

Sources & evidence

ORD record
ord-8179ef524ffd4efc91a5d8ef649b1609
Source dataset
uspto-grants-2013_10
Patent number
US08562693B2

Reaction notes

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