2-Nitro-1-(prop-2-ynyl)-1H-imidazole → 1-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)-3-(tosyloxy)propan-2-yl acetate

HRID 1157085Notes

Reaction equation

HRID 1157085 reaction equation
[N+:1]([C:4]1[N:5]([CH2:9][C:10]#[CH:11])[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[C:12]([O:15][CH:16]([CH2:21][O:22][S:23]([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH2:17][N:18]=[N+:19]=[N-:20])(=[O:14])[CH3:13]>>[C:12]([O:15][CH:16]([CH2:21][O:22][S:23]([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH2:17][N:18]1[CH:11]=[C:10]([CH2:9][N:5]2[CH:6]=[CH:7][N:8]=[C:4]2[N+:1]([O-:3])=[O:2])[N:20]=[N:19]1)(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 546751432-Nitro-1-(prop-2-ynyl)-1H-imidazoleHCID 575402081-Azido-3-(tosyloxy)propan-2-yl acetate

Product 1

HCID 595110471-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)-3-(tosyloxy)propan-2-yl acetate

Procedure

2-Nitro-1-(prop-2-ynyl)-1H-imidazole 10 (0.2 g, 1.32 mmol) is heated with 1-azido-3-(tosyloxy)propan-2-yl acetate 15 (0.41 g, 1.32 mmol) at 60° C. overnight. The residue is purified by chromatography on silica gel (MeOH/CH2Cl2, 1:10) to afford 16.

Workup

  1. customThe residue is purified by chromatography on silica gel (MeOH/CH2Cl2, 1:10)

Sources & evidence

ORD record
ord-76352d8b2b2a424e844950bb39d98cd1
Source dataset
uspto-grants-2010_10
Patent number
US07807394B2

Reaction notes

Loading…