1H-1,2,4-Triazole → HCID 10135293, compound

HRID 2183927Notes

Reaction equation

HRID 2183927 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].Br[CH2:9][C:10]1[CH:15]=[CH:14][N:13]2[C:16]([C:19]3[CH:20]=[CH:21][C:22]([F:33])=[C:23]([C:25]4[C:26]([C:31]#[N:32])=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:24]=3)=[CH:17][N:18]=[C:12]2[N:11]=1>CN(C)C=O>[F:33][C:22]1[CH:21]=[CH:20][C:19]([C:16]2[N:13]3[CH:14]=[CH:15][C:10]([CH2:9][N:1]4[CH:5]=[N:4][CH:3]=[N:2]4)=[N:11][C:12]3=[N:18][CH:17]=2)=[CH:24][C:23]=1[C:25]1[C:26]([C:31]#[N:32])=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 69708935HCID 69708935, compound

Product 1

HCID 10135293HCID 10135293, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1H-[1,2,4]triazole (30 mg, 0.435 mmol) in N,N-dimethylformamide was added sodium hydride (17 mg, 0.435 mmol) as a 60% dispersion in oil and the reaction stirred at ambient temperature for 0.5 h. To this mixture was added the previously prepared solution of 5′-(7-bromomethylimidazo[1,2-α]pyrimidin-3-yl)-2′-fluorobiphenyl-2-carbonitrile in N,N-dimethylformamide in a dropwise manner. This mixture was allowed to stir at ambient temperature for 16 h before removal of the reaction solvent in vacuo. The residue was purified by silica gel chromatography eluting with a mixture of dichloromethane, methanol and ammonia (90:5:0.5) to give 2′-fluoro-5′-[7-([1,2,4]triazol-1-ylmethyl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile: δH (360 MHz, CDCl3) 5.57 (2H, s), 6.89 (1H, d, J 7.1), 7.41 (3H, t, J 9.5 ), 7.52-7.62 (4H, m), 7.68-7.73 (1H, m), 7.82-7.85 (1H, m), 7.92 (1H, s), 8.01 (1H, s), 8.32 (1H, s), 8.80 (1H, s); m/z (ES+) 396 (M++H).

Workup

  1. stirringto stir at ambient temperature for 16 h before removal of the reaction solvent in vacuo
  2. customThe residue was purified by silica gel chromatography
  3. washeluting with a mixture of dichloromethane, methanol and ammonia (90:5:0.5)

Sources & evidence

ORD record
ord-dbdd5bdc91064e04a7803d92dcb81aba
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

Loading…