Trifluoroacetic acid → HCID 44137942, compound

HRID 517824Notes

Reaction equation

HRID 517824 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][NH:14][C:15](=[O:22])[O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19].C(N(CC)CC)C.Cl.[CH3:31][N:32]1[CH2:37][CH2:36][C:35](=O)[CH2:34][CH2:33]1.C(O)(C(F)(F)F)=O>Cl.C(O)C>[CH3:31][N:32]1[CH2:37][CH2:36][C:35]2[N:8]([CH2:12][CH2:13][NH:14][C:15](=[O:22])[O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19])[C:5]3[CH:4]=[CH:3][C:2]([CH3:10])=[CH:7][C:6]=3[C:34]=2[CH2:33]1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 122100571-Methylpiperidin-4-one hydrochlorideHCID 59161649HCID 59161649, compound

Product 1

HCID 44137942HCID 44137942, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 21887872Ethanol hydrochlorideSolvent

Procedure

Preparation of the title compound was carried out using p-Tolylhydrazine hydrochloride (396 mg, 2.5 mmol), 2,2,2-trichloroethyl 2-bromoethylcarbamate (750 mg, 2.5 mmol), triethylamine (1 ml, 7.4 mmol) and N-methyl-4-piperidone hydrochloride (394 mg, 2.6 mmol) in ethanol-HCl (15 ml) to obtain 160 mg of 2,2,2-trichloroethyl 2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)ethylcarbamate as TFA salt after purification on silica gel (230-400 mesh) chromatography eluting with methanol-dichloromethane gradient followed by reverse-phase chromatography (C-18, 500 mm×50 mm, Mobile Phase A=0.05% TFA in water, B=0.05% TFA in acetonitrile, Gradient: 10% B to 80% B in 30 min, injection vol. 5 mL).

Sources & evidence

ORD record
ord-4c5eecea56074bd5a1c2aa51e8558b49
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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