Triethylamine → HCID 68560693, compound

HRID 1045580Notes

Reaction equation

HRID 1045580 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][CH:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)O)[C:6]3[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26][C:5]=3[C:4]=2[CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[OH-].[K+]>C(Cl)Cl.O.CN1C(=O)CCC1>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([CH:12]=[CH:11][N:7]2[C:8]3[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][C:4]=3[C:5]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22][C:6]2=3)=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 31297Methanesulfonyl chlorideHCID 59368380HCID 59368380, compound

Product 1

HCID 68560693HCID 68560693, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

The title compound was prepared by following general procedure 6. To a solution of 2-(9-chloro-3-methyl-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)-1-(4-methoxyphenyl)ethanol (100 mg, 0.25 mmol) in DCM (2 mL), triethylamine (0.053 mL, 0.38 mmol) was added and stirred for 10 min., methane sulfonyl chloride (0.02 mL, 0.27 mmol) was added slowly at 0° C. and stirred at the same temperature for 1 h and stirred at RT for 2 h. The reaction mixture was diluted with water, extracted with DCM. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography. Pure product was taken into NMP (2.0 mL), KOH powder (72 mg, 1.2 mmol) was added at RT and heated at 80° C. for 24 h. The product was detected by LCMS, the reaction mixture was diluted with water, extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, concentrated and crude product was purified by reverse phase chromatography to get 6 mg of pure product as the TFA salt.

Workup

  1. stirringstirred at the same temperature for 1 h
  2. stirringstirred at RT for 2 h
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by column chromatography
  7. additionwas added at RT
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. customcrude product was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-6835b7fd1e2b467cbb5c82f2c3cd1386
Source dataset
uspto-grants-2013_10
Patent number
US08569287B2

Reaction notes

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