Sodium Hydroxide → HCID 59368251, compound

HRID 1481406Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15][C:5]=3[C:4]=2[CH:3]=1.[OH-].[Na+].[Cl:19][C:20]1[CH:21]=[N:22][CH:23]=[C:24]([CH:26]=[CH2:27])[CH:25]=1>O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:27][CH2:26][C:24]3[CH:23]=[N:22][CH:21]=[C:20]([Cl:19])[CH:25]=3)[C:6]3[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15][C:5]=3[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

The title compound was prepared by following general procedure 4. To a solution of 9-chloro-3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (100 mg, 0.42 mmol) in 50% aq. NaOH solution (5 mL) tetra n-butyl ammonium chloride (9 mg, 0.03 mmol) followed by 3-chloro-5-vinylpyridine (65 mg, 0.47 mmol) was added. The reaction mixture was heated at 60° C. for 8 h. After completion of reaction, the reaction mixture was diluted with water, extracted with ethyl acetate; the organic layer was dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by reverse phase chromatography to afford 5 mg of 9-chloro-6-(2-(5-chloropyridin-3-yl)ethyl)-3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole as the TFA salt.

Workup

customThe title compound was prepared
additionwas added
customAfter completion of reaction
extractionextracted with ethyl acetate
dry with materialthe organic layer was dried over Na2SO4
concentrationconcentrated under reduced pressure
customThe crude product was purified by reverse phase chromatography

Sources & evidence

ORD record: ord-350c45e8db6c47998f1ddce38abf51cd
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409910B2

Reaction notes

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