Triethylamine → HCID 23445073, compound

HRID 433565Notes

Reaction equation

[H-].[Na+].[CH3:3][C:4]1[NH:5][CH:6]=[CH:7][N:8]=1.Cl.[Cl:10][CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[CH:17]=1.C(N(CC)CC)C>CN(C=O)C>[ClH:10].[Cl:25][C:20]1[CH:19]=[C:18]([C:16]2[CH:15]=[N:14][CH:13]=[C:12]([CH2:11][N:5]3[CH:6]=[CH:7][N:8]=[C:4]3[CH3:3])[CH:17]=2)[CH:23]=[CH:22][C:21]=1[Cl:24]

Participants

Conditions

Temperature: 20 °C

Procedure

To a suspension of sodium hydride (17 mg of a 55% dispersion in mineral oil, 0.39 mmol) in DMF (5 ml) was added 2-methylimidazole (32 mg, 0.39 mmol). This mixture was stirred for 1.5 h at 20° C. Following this, 3-chloromethyl-5-(3,4-dichloro-phenyl)-pyridine hydrochloride (1:1) (100 mg, 0.32 mmol) and triethylamine (78 mg, 0.78 mmol) were added and the mixture heated to 100° C. for 4 h. After cooling, the DMF was evaporated and the residue was directly chromatographed [silica, elution with CH2Cl2/(2M NH3 in MeOH)=85:15] to afford the free base of the title compound as a yellow oil. This material was dissolved in MEOH, cooled to 4° C. with stirring and treated with HCl/EtOH (1.46 M 1.1 eq) for 15 min. Evaporation of the solvent and drying under high vacuum at 50° C., for 2 h afforded the title compound (71 mg, 62%) as a light yellow solid. MS: m/e=317.1 (M+)

Workup

additionwere added
temperaturethe mixture heated to 100° C. for 4 h
temperatureAfter cooling
customthe DMF was evaporated
customthe residue was directly chromatographed
wash[silica, elution with CH2Cl2/(2M NH3 in MeOH)=85:15]

Sources & evidence

ORD record: ord-fbc0ade591b6429a8ba684504ed7aeff
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06667335B2

Reaction notes

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