HCID 11053853, compound → HCID 57876136, compound

HRID 1465361Notes

Reaction equation

HRID 1465361 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:11][CH2:12][C:13]2[CH:14]=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=2)N)=[CH:5][CH:4]=1.[F:20][C:21]([F:36])([F:35])[C:22]1[CH:23]=[C:24]([N:28]2[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]2)[CH:25]=[CH:26][CH:27]=1>C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]2[N:9]([CH2:11][CH2:12][C:13]3[CH:14]=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=3)[C:31]3[CH2:32][CH2:33][N:28]([C:24]4[CH:25]=[CH:26][CH:27]=[C:22]([C:21]([F:36])([F:20])[F:35])[CH:23]=4)[CH2:29][C:30]=3[C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 11053853HCID 11053853, compoundHCID 68731816HCID 68731816, compound

Product 1

HCID 57876136HCID 57876136, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of N-(4-Chloro-phenyl)-N-[2-(6-methyl-pyridin-3-yl)-ethyl]-hydrazine hydrochloride (0.13 g, 0.5 mmol) in absolute ethanol (5 mL) was added 1-(3-Trifluoromethyl-phenyl)-piperidin-4-one (0.122 g, 0.5 mmol) at RT and then refluxed for 1 h. After completion (TLC), ethanol was evaporated. The crude was purified by preparative HPLC to provide desired compound as brown colored solid (0.02 g, 10% yield) 8-Chloro-5-[2-(6-methyl-pyridin-3-yl)-ethyl]-2-(3-trifluoromethyl-phenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (0.020 g, 0.0425 mmol) was dissolved in THF (1.0 mL). A solution of oxalic acid dihydrate (0.0053 g, 0.0425 mmol) in 1.5 mL THF was added and stirred for 30 min at RT. Precipitate was filtered and dried to give oxalate salt as brown solid (0.01 g, 43% yield).

Workup

  1. temperaturerefluxed for 1 h
  2. customAfter completion (TLC), ethanol was evaporated
  3. customThe crude was purified by preparative HPLC

Sources & evidence

ORD record
ord-acef4f19e8a34203a300a5cda54da924
Source dataset
uspto-grants-2015_04
Patent number
US08999978B2

Reaction notes

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