Sodium hydride → HCID 21216884, compound

HRID 1586599Notes

Reaction equation

HRID 1586599 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[NH:9][C:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][C:17]([O:23][CH3:24])=[CH:18][CH:19]=5)[C:14]=4[C:13]4[C:25](=[O:30])[N:26]([CH3:29])[C:27](=[O:28])[C:12]=4[C:11]=3[C:5]=2[CH:4]=1.[H-].[Na+].[CH3:33][N:34]([CH3:39])[CH2:35][CH2:36][CH2:37]Cl.C(OC(C)C)(C)C.C(OCC)(=O)C>CN(C)C=O>[CH3:33][N:34]([CH3:39])[CH2:35][CH2:36][CH2:37][N:9]1[C:10]2[C:22]3[NH:21][C:20]4[CH:19]=[CH:18][C:17]([O:23][CH3:24])=[CH:16][C:15]=4[C:14]=3[C:13]3[C:25](=[O:30])[N:26]([CH3:29])[C:27](=[O:28])[C:12]=3[C:11]=2[C:5]2[C:6]1=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 212168326,7,12,13-tetrahydro-3,9-dimethoxy-6-methyl-5,7-dioxo-5H-indolo[2,3-a]-pyrrolo[3,4-c]carbazoleHCID 22281796Diisopropylether ethyl acetate

Product 1

HCID 21216884HCID 21216884, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 2.0 g (5 mmol) 6,7,12,13-tetrahydro-3,9-dimethoxy-6-methyl-5,7-dioxo-5H-indolo[2,3-a]-pyrrolo[3,4-c]carbazole in 100 ml dry dimethylformamide is added dropwise at 20° C. to a suspension of 182 mg (6.1 mmol) sodium hydride (80% in paraffin oil) in 5 ml dimethylformamide. After stirring for 1 hour at 20° C. 738 mg (6.1 mmol) 3-dimethylaminopropyl chloride are added thereto and the reaction mixture is stirred for 20 hours at 20° C. The solvent is distilled off in a vacuum, the residue is mixed with 150 ml ethyl acetate and 150 ml of water and the solid material insoluble in both phases is filtered off. The solid material is taken up in tetrahydrofuran, the tetrahydrofuran solution is washed with a saturated sodium chloride solution, dried over anhydrous sodium sulphate, filtered and evaporated. The residue, together with the residue from the ethyl acetate solution, is chromatographed on silica gel with ethyl acetate/methanol (4:1 v/v). The fraction with the Rf 0.2 in ethyl acetate/methanol (3:1 v/v) is isolated and stirred with diisopropyl ether/ethyl acetate (9:1 v/v). The crystals formed are filtered off. 12-(3-Dimethylaminopropyl)-6,7,12,13-tetrahydro-3,9-dimethoxy-6-methyl-5,7-dioxo-5H-indolo-[2,3-a]pyrrolo[3,4-c]carbazole is obtained in the form of yellow-brown crystals.

Workup

  1. stirringthe reaction mixture is stirred for 20 hours at 20° C
  2. distillationThe solvent is distilled off in a vacuum
  3. additionthe residue is mixed with 150 ml ethyl acetate and 150 ml of water
  4. filtrationthe solid material insoluble in both phases is filtered off
  5. washthe tetrahydrofuran solution is washed with a saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue, together with the residue from the ethyl acetate solution, is chromatographed on silica gel with ethyl acetate/methanol (4:1 v/v)
  10. customThe fraction with the Rf 0.2 in ethyl acetate/methanol (3:1 v/v) is isolated
  11. customThe crystals formed
  12. filtrationare filtered off

Sources & evidence

ORD record
ord-2d60ea567b49459b9f4a15b35a96f4ad
Source dataset
uspto-grants-1999_08
Patent number
US05945440

Reaction notes

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