2-[1-(triphenylmethyl)-1H-imidazol-4-yl]pyridine-4-carbonitrile → HCID 178510201, compound

HRID 2277473Notes

Reaction equation

HRID 2277473 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][N:14]=3)[N:10]=[CH:9]2)C=CC=CC=1>C(O)(=O)C>[NH:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][N:14]=2)[N:10]=[CH:9]1

Participants

3

Reactant 1

HCID 904076602-[1-(triphenylmethyl)-1H-imidazol-4-yl]pyridine-4-carbonitrile

Product 1

HCID 178510201HCID 178510201, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-[1-(triphenylmethyl)-1H-imidazol-4-yl]pyridine-4-carbonitrile (510 mg, 1.2 mmol) in acetic acid (10 ml) was heated at 90° C. for 18 hr. Reaction mixture was purified by ISCO flash column chromatography (EtOAc/Hexane=0-100%) to get 130 mg of product. Some starting material was recovered and heated in acetic acid again overnight at 90° C. Additional product was obtained to give total 160 mg product as light yellow solid (78%). 1H NMR (400 MHz, DMSO-d6): δ 7.62 (1H, dd, J=1.2 Hz and 4.9 Hz), 7.81 (2H, s), 8.13 (1H, s), 8.73 (1H, d, J=4.8 Hz). [M+H] Calc'd for C9H6N4, 171. Found, 171.

Workup

  1. customReaction mixture
  2. customwas purified by ISCO flash column chromatography (EtOAc/Hexane=0-100%)

Sources & evidence

ORD record
ord-260584e0cc2243448db8b40bba2bb221
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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