Triethylamine → HCID 59368363, compound

HRID 1481470Notes

Reaction equation

HRID 1481470 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])=[C:16]([O:22][CH3:23])[CH:15]=3)O)[C:6]3[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28][C:5]=3[C:4]=2[CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[OH-].[K+]>C(Cl)Cl.O.CO>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7](/[CH:11]=[CH:12]/[C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=3)[C:6]3[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28][C:5]=3[C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 31297Methanesulfonyl chlorideHCID 59368505HCID 59368505, compound

Product 1

HCID 59368363HCID 59368363, compoundYield 6.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-(9-chloro-3-methyl-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)-1-(3,4-dimethoxyphenyl)ethanol (300 mg, 0.722 mmol) in DCM (5 mL), triethylamine (0.15 mL, 1.077 mmol) were added and stirred for 10 min., methane sulfonyl chloride (0.062 mL, 0.795 mmol) was added slowly at 0° C. and stirred at the same temperature for 1 h, then at RT for 2 h. Reaction mixture was diluted with water, extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography. The pure product was dissolved in NMP (2.0 mL), KOH powder (283 mg, 5.06 mmol) was added at RT and heated at 90° C. for 14 h. Product was detected by LCMS. The reaction mixture was diluted with methanol, filtered and evaporated. Crude product was purified by reverse phase chromatography to get 18 mg of pure product as TFA salt. 1H NMR (DMSO-d6, TFA salt) δ (ppm): 7.80-7.60 (m, 2H), 7.35 (s, 1H), 7.30-7.20 (d, 1H), 7.20-7.15 (d, 1H), 7.00-6.90 (d, 1H), 6.80-6.70 (m, 2H), 3.90 (s, 3H), 3.85 (s, 3H), 3.80-3.60 (m, 2H), 2.95 (s, 3H), 2.90-2.80 (m, 2H), 2.60-2.30 (m, 4H).

Workup

  1. stirringstirred at the same temperature for 1 h
  2. waitat RT for 2 h
  3. customReaction mixture
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by column chromatography
  8. dissolutionThe pure product was dissolved in NMP (2.0 mL)
  9. filtrationfiltered
  10. customevaporated
  11. customCrude product was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-635e9df0c72a46298da05e455bd66c73
Source dataset
uspto-grants-2016_08
Patent number
US09409910B2

Reaction notes

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