Triethylamine → 247082-25-3

HRID 2187043Notes

Reaction equation

HRID 2187043 reaction equation
[CH3:1][NH:2][C:3]([CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2[CH2:15][CH2:16][NH:17][CH2:18][C:7]1=2)=[O:4].F[C:20](F)(F)[C:21]([O-])=O.BrCCCC[N:31]1[C:39]2[CH:38]=[CH:37][CH:36]=[C:35]3[CH2:40][CH2:41][CH2:42][C@@H:33]([C:34]=23)[C:32]1=[O:43].[CH2:44](N(CC)CC)[CH3:45].C(OCC)(=O)C>CN(C)C=O>[CH3:1][NH:2][C:3]([CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2[CH2:15][CH2:16][N:17]([CH2:44][CH2:45][CH2:20][CH2:21][C@@:33]34[CH2:42][CH2:41][CH2:40][C:35]5[C:34]3=[C:39]([CH:38]=[CH:37][CH:36]=5)[NH:31][C:32]4=[O:43])[CH2:18][C:7]1=2)=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 70153863HCID 70153863, compoundHCID 86758195HCID 86758195, compound

Product 1

HCID 15489027247082-25-3Yield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9-methylcarbamoylmethyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole•trifluoroacetate (450 mg, 1.26 mmol) and (S)-(4-bromobutyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (308 mg, 1.0 mmol) were dissolved in dimethylformamide (5 ml). Then triethylamine(0.9 ml, 6 mmol) was added thereto. The resulting solution was reacted at room temperature for 3 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 obtain a crude reaction product, which was purifiedbymeans of silica gel column chromatography, whereby 376 mg (yield 80%) of the above-described object compound could be obtained.

Workup

  1. customThe resulting solution was reacted at room temperature for 3 days
  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. customto obtain a crude
  7. customreaction product, which

Sources & evidence

ORD record
ord-dcf4f2e913e6442dbace3c4bd7787dd2
Source dataset
uspto-grants-2002_06
Patent number
US06407112B1

Reaction notes

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