Dimethylamine → HCID 22556677, compound

HRID 983998Notes

Reaction equation

HRID 983998 reaction equation
O[CH2:2][CH:3]1[CH2:12][C:11]2[C:6]3=[C:7]([C:13]([C:15]4[C:16](=[O:30])[NH:17][C:18](=[O:29])[C:19]=4[C:20]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[NH:22][CH:21]=4)=[CH:14][N:5]3[CH2:4]1)[CH:8]=[CH:9][CH:10]=2.CS(OS(C)(=O)=O)(=O)=O.N1C=CC=CC=1.[CH3:46][NH:47][CH3:48]>O1CCCC1.C(OCC)(=O)C>[CH3:46][N:47]([CH2:2][CH:3]1[CH2:12][C:11]2[C:6]3=[C:7]([C:13]([C:15]4[C:16](=[O:30])[NH:17][C:18](=[O:29])[C:19]=4[C:20]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[NH:22][CH:21]=4)=[CH:14][N:5]3[CH2:4]1)[CH:8]=[CH:9][CH:10]=2)[CH3:48]

Participants

7

Reactant 4

HCID 674Dimethylamine2×HCID 1049PyridineHCID 81560Methanesulfonic anhydrideHCID 10272122HCID 10272122, compound

Product 1

HCID 22556677HCID 22556677, compoundYield 106.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 3-(5-hydroxymethyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrole-2,5-dione (0.335 g, 0.84 mmol) and methylsulfonic acid anhydride (0.3 g, 1.7 mmol) in tetrahydrofuran was added pyridine (0.245 mL, 3.4 mmol). The mixture was heated to reflux for 4.5 h, cooled to room temperature, diluted with ethyl acetate, washed with water and saturated aqueous sodium chloride. The organic layer was dried over sodium sulfate, filtered and concentrated to give an oil, which was used in the next step without further purification. The crude mesylate was dissolved in tetrahydrofuran (9 mL), then dimethylamine aqueous solution (40%, 4.22 ml, 33.6 mmol) was added. After stirring for 24 hours at room temperature, additional dimethylamine aqueous solution (40%,4.22 mL, 33.6 mmol) was added, and the mixture stirred for an additional 48 hours. The mixture was diluted with ethyl acetate, washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to provide 0.38 g of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4.5 h
  3. washwashed with water and saturated aqueous sodium chloride
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil, which
  8. customwas used in the next step without further purification
  9. dissolutionThe crude mesylate was dissolved in tetrahydrofuran (9 mL)
  10. stirringthe mixture stirred for an additional 48 hours
  11. washwashed with water
  12. dry with materialdried over sodium sulfate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-300f78e7498648ee854a330813d70d1c
Source dataset
uspto-grants-2005_03
Patent number
US06867198B2

Reaction notes

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