Dimethylformamide → HCID 22080927, compound

HRID 2187044Notes

Reaction equation

HRID 2187044 reaction equation
C(OCC[CH:7]1[C:12]2[NH:13][C:14]3[C:19]([C:11]=2[CH2:10][CH2:9][NH:8]1)=[CH:18][CH:17]=[CH:16][CH:15]=3)(=O)C.F[C:21](F)(F)[C:22]([O-:24])=O.N1[C:35]2[CH:34]=[CH:33][CH:32]=[C:31]3[CH2:36][CH2:37][CH2:38][CH:29]([C:30]=23)[C:28]1=O.C(=O)([O-])[O-].[K+].[K+].[C:46](OCC)(=O)[CH3:47].[CH3:52][N:53](C)[CH:54]=[O:55]>>[OH:24][CH2:22][CH2:21][N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]2[CH2:10][CH2:9][N:8]([CH2:35][CH2:34][CH2:33][CH2:32][C@@:31]34[CH2:36][CH2:37][CH2:38][C:29]5[C:30]3=[C:52]([CH:46]=[CH:47][CH:28]=5)[NH:53][C:54]4=[O:55])[CH2:7][C:12]1=2

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 5993752a,3,4,5-Tetrahydrobenzo[cd]indol-2(1H)-oneHCID 86758196HCID 86758196, compound

Product 1

HCID 22080927HCID 22080927, compoundYield 76%

Procedure

(2-acetoxy)ethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole•trifluoroacetate (230 mg, 0.73 mmol) and (S)-4-bromobutyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (185 mg, 0.6 mmol) were dissolved in dimethylformamide (5 ml). Then anhydrous potassium carbonate (280 mg, 2 mmol) was added thereto. The resulting reaction mixture was stirred at room temperature for 2 days. To the reaction mixture obtained was added ethyl acetate (50 ml), which was then washed with water (50 ml×2) and saturated saline solution, successively dried with anhydrous sodium sulfate. The ethyl acetate solution was concentrated under reduced pressure. To the resulting product were added methanol (30 ml) and triethylamine (3 ml), which was heated at 50° C. for 5 hours and then subjected to concentration again under reduced pressure to obtain a crude reaction product. Silica gel column chromatography was applied to purify the same, whereby 246 mg (yield 76%) of the above-described object compound could be obtained.

Workup

  1. customThe resulting reaction mixture
  2. customTo the reaction mixture obtained
  3. washwas then washed with water (50 ml×2) and saturated saline solution
  4. dry with materialsuccessively dried with anhydrous sodium sulfate
  5. concentrationThe ethyl acetate solution was concentrated under reduced pressure
  6. additionTo the resulting product were added methanol (30 ml) and triethylamine (3 ml), which
  7. temperaturewas heated at 50° C. for 5 hours
  8. concentrationsubjected to concentration again under reduced pressure
  9. customto obtain a crude
  10. customreaction product

Sources & evidence

ORD record
ord-3ac709294a2a4b2f8d1fe9daf43243e7
Source dataset
uspto-grants-2002_06
Patent number
US06407112B1

Reaction notes

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