Sodium hydride → HCID 66835962, compound

HRID 2404461Notes

Reaction equation

HRID 2404461 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].Cl[CH2:9][CH2:10][CH2:11][C:12]#[C:13][C:14]1[CH:15]=[C:16]([CH:20]([O:30][CH:31]2[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]2)[C:21]2[NH:25][C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[N:22]=2)[CH:17]=[CH:18][CH:19]=1>CN(C=O)C>[CH3:37][N:34]1[CH2:35][CH2:36][CH:31]([O:30][CH:20]([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:13]#[C:12][CH2:11][CH2:10][CH2:9][N:2]3[N:3]=[CH:4][CH:5]=[N:1]3)[CH:15]=2)[C:21]2[NH:22][C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[N:25]=2)[CH2:32][CH2:33]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66836006HCID 66836006, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 66835962HCID 66835962, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,2,3-triazole (66 mg) in DMF (0.6 mL) is added sodium hydride (25 mg). After gas evolution ceased, 2-[[3-(5-chloropent-1-ynyl)phenyl](1-methylpiperidin-4-yloxy)methyl]-1H-benzimidazole (50 mg) and a catalytic quantity of n-tetrabutylammonium iodide are added. After stirring overnight at room temperature, the solvent is removed under reduced pressure to dryness. The residue is purified by chromatography (dichloromethane/methanol/ammonia 90/10/1) to afford 2-{(1-methylpiperidin-4-yloxy)[3-(5-[1,2,3]triazol-2-yl-pent-1-ynyl)phenyl]methyl}-1H-benzimidazole.

Workup

  1. customthe solvent is removed under reduced pressure to dryness
  2. customThe residue is purified by chromatography (dichloromethane/methanol/ammonia 90/10/1)

Sources & evidence

ORD record
ord-08c0a9ea9eaf4e358f2a24a9ca26e99f
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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