Triethylamine hydrochloride → HCID 178482563, compound

HRID 1808151Notes

Reaction equation

[C:1]([CH:3]([N:14]([CH:21]1[CH2:26][CH2:25][C:24]([N:33]([CH3:35])[CH3:34])([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:23][CH2:22]1)[C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)#[N:2].[N-:36]=[N+:37]=[N-:38].[Na+].Cl.C(N(CC)CC)C>CN(C)C=O.C1(C)C=CC=CC=1>[NH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([CH2:4][CH:3]([N:14]([CH:21]2[CH2:22][CH2:23][C:24]([N:33]([CH3:34])[CH3:35])([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:25][CH2:26]2)[C:15](=[O:20])[C:16]([F:19])([F:17])[F:18])[C:1]2[NH:38][N:37]=[N:36][N:2]=2)=[CH:6]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of N-[1-cyano-2-(1H-indol-3-yl)ethyl]-N-(4-dimethylamino-4-phenylcyclohexyl)-2,2,2-trifluoroacetamide (polar diastereomer) (613 mg, 1.27 mmol) in N,N-dimethylformamide (5 mL) and toluol (5 mL) was mixed with sodium azide (825 mg, 12.7 mmol) and triethylamine hydrochloride (1.74 g, 12.7 mmol) and stirred for 2 d at 80° C. in a Teflon pressure vessel. The solvent was then concentrated to low volume in a vacuum, the residue repeatedly mixed with toluol and the solution again concentrated to low volume in a vacuum each time. The raw product (1.62 g) was purified by flash chromatography (200 g, 20×4; 1 cm) with dichloromethane/methanol [2:1+1% NH3 (32% in H2O)].

Workup

concentrationThe solvent was then concentrated to low volume in a vacuum
additionthe residue repeatedly mixed with toluol
concentrationthe solution again concentrated to low volume in a vacuum each time
customThe raw product (1.62 g) was purified by flash chromatography (200 g, 20×4; 1 cm) with dichloromethane/methanol [2:1+1% NH3 (32% in H2O)]

Sources & evidence

ORD record: ord-da280471655e4564915abc1fd2563e09
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357705B2

Reaction notes

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