Triethylamine → HCID 68561241, compound

HRID 1481457Notes

Reaction equation

HRID 1481457 reaction equation
[CH3:1][N:2]1[CH2:15][CH2:14][C:13]2[C:12]3[CH:11]=[C:10]([CH3:16])[CH:9]=[CH:8][C:7]=3[N:6]([CH2:17][CH:18]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)O)[C:5]=2[CH2:4][CH2:3]1.C(N(CC)CC)C.CS(Cl)(=O)=O.[OH-].[K+]>C(Cl)Cl.CO>[F:26][C:23]1[CH:22]=[CH:21][C:20]([CH:18]=[CH:17][N:6]2[C:7]3[CH:8]=[CH:9][C:10]([CH3:16])=[CH:11][C:12]=3[C:13]3[CH2:14][CH2:15][N:2]([CH3:1])[CH2:3][CH2:4][C:5]2=3)=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 31297Methanesulfonyl chlorideHCID 59368226HCID 59368226, compound

Product 1

HCID 68561241HCID 68561241, compoundYield 7.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
90 °C

Procedure

To a solution of 2-(3,9-dimethyl-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)-1-(4-fluorophenyl)ethanol (150 mg, 0.42 mmol) in DCM (7 mL), triethylamine (0.088 mL, 0.63 mmol) was added and stirred for 10 min, methane sulfonyl chloride (0.036 mL, 0.47 mmol) were added slowly at 0° C. and stirred at RT for 2 h. Reaction was monitored by TLC. The reaction mixture was diluted with DCM and washed with water. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. Crude product was dissolved in NMP (0.8 mL), KOH powder (166 mg, 2.97 mmol) was added at RT and heated at 90° C. for 14 h. Reaction was monitored by LCMS. The reaction mixture was diluted with methanol, inorganic material was filtered off and the compound was purified by reverse phase chromatography to afford 10 mg of product as the TFA salt. 1H NMR (CD3OD, TFA salt) δ (ppm): 7.70-7.50 (m, 4H), 7.30 (s, 1H), 7.20-7.00 (m, 3H), 6.80-6.70 (d, 1H), 3.90-3.75 (m, 4H), 3.50-3.40 (m, 4H), 3.15 (s, 3H), 2.35 (s, 3H).

Workup

  1. stirringstirred at RT for 2 h
  2. customReaction
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. dissolutionCrude product was dissolved in NMP (0.8 mL)
  7. customReaction
  8. filtrationwas filtered off
  9. customthe compound was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-4cea8cbef8c848d3b0928fd5c8d8e1ef
Source dataset
uspto-grants-2016_08
Patent number
US09409910B2

Reaction notes

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