Sodium Iodide → HCID 58399240, compound

HRID 1927226Notes

Reaction equation

HRID 1927226 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[C:6]1[C:7]([NH2:13])=[N:8][C:9]([NH2:12])=[CH:10][CH:11]=1.[CH2:14]([O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[I-].[Na+].[H-].[Na+]>O.CN(C=O)C>[CH2:14]([O:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:26][N:3]2[N:2]=[N:1][C:5]([C:6]3[C:7]([NH2:13])=[N:8][C:9]([NH2:12])=[CH:10][CH:11]=3)=[N:4]2)=[CH:28][CH:29]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 700424-Benzyloxybenzyl chlorideHCID 59287388HCID 59287388, compound

Product 1

HCID 58399240HCID 58399240, compoundYield 20.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

3-(2H-tetrazol-5-yl)-pyridin-2,6-diamine (60 mg) described in Manufacturing Example 7-3, 4-benzyloxybenzyl chloride (79 mg), sodium iodide (51 mg), NaH (14 mg, 60% in oil), and DMF (0.69 mL) were stirred for 10 minutes at 60° C. Water was added to the reaction solution, which was then extracted with ethyl acetate. The organic layer was concentrated and purified by NH silica gel column chromatography (hexane:ethyl acetate=2:1, then ethyl acetate). Ethyl acetate-hexane was added to the residue thus obtained, and the solids were filtered off to obtain the titled compound (26 mg).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. custompurified by NH silica gel column chromatography (hexane
  4. additionEthyl acetate-hexane was added to the residue
  5. customthus obtained
  6. filtrationthe solids were filtered off

Sources & evidence

ORD record
ord-1959fcb6c5144a11ae259d164db1380c
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

Loading…