Sodium Iodide → HCID 24882978, compound

HRID 1927222Notes

Reaction equation

HRID 1927222 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:9]=[C:8]([NH2:10])[C:7]([C:11]2[N:12]=[N:13][NH:14][N:15]=2)=[CH:6][CH:5]=1.[CH2:16]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[I-].[Na+].[H-].[Na+]>C(OCC)(=O)C.CCCCCC.O.CN(C=O)C>[CH2:16]([O:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:28][N:14]2[N:13]=[N:12][C:11]([C:7]3[C:8]([NH2:10])=[N:9][C:4]([CH2:3][O:2][CH3:1])=[CH:5][CH:6]=3)=[N:15]2)=[CH:30][CH:31]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 700424-Benzyloxybenzyl chlorideHCID 59287395HCID 59287395, compound

Product 1

HCID 24882978HCID 24882978, compoundYield 12.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
60 °C

Procedure

6-Methoxymethyl-3-(2H-tetrazol-5-yl)-pyridin-2-ylamine (50 mg) described in Manufacturing Example 6-3, 4-benzyloxybenzyl chloride (57 mg), sodium iodide (36 mg), NaH (9.7 mg/60% in oil), and DMF (3 mL) were stirred for 15 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). The residue thus obtained was solidified with ethyl acetate-hexane to obtain the titled compound (12 mg).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. custompurified by NH silica gel column chromatography (hexane:ethyl acetate=2:1)
  4. customThe residue thus obtained

Sources & evidence

ORD record
ord-400759e6ed0149899ca3c03ea74c1cee
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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