Potassium Cyanide → HCID 58276302, compound

HRID 70342Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][CH2:11][C:12]2[O:16][C:15]([C:17]3[CH:27]=[CH:26][C:20]([C:21](OCC)=[O:22])=[CH:19][CH:18]=3)=[CH:14][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[C-]#[N:29].[K+]>CO.N>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][CH2:11][C:12]2[O:16][C:15]([C:17]3[CH:27]=[CH:26][C:20]([C:21]([NH2:29])=[O:22])=[CH:19][CH:18]=3)=[CH:14][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 125 °C

Procedure

To a 50 mL sealed tube was added ethyl 4-[5-({[2-(3-fluorophenyl)ethyl]amino}methyl)-2-furanyl]benzoate (100 mg, 0.27 mmol, Example X-1), 2.0 M MeOH/NH3 (20 mL), and KCN (30 mg). The reaction mixture was stirred at 125° C. overnight. The crude mixture was purified on RP-preparative HPLC to give 3 mg of 4-[5-({[2-(3-fluorophenyl)ethyl]amino}methyl)-2-furanyl]benzamide. (M+1) 339.23, 1.42 min (LC/MS method A)

Workup

customTo a 50 mL sealed tube
customThe crude mixture was purified on RP-preparative HPLC

Sources & evidence

ORD record: ord-dbf83c691ef945f0a44c6e85bc2fbd2c
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822518B2

Reaction notes

Loading…