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Sodium Iodide → HCID 24882977, compound

HRID 1927220
Notes
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Reaction equation

HRID 1927220 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[C:6]1[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][CH:11]=1.[CH2:13]([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[I-].[Na+].[H-].[Na+]>O.CN(C=O)C>[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:25][N:3]2[N:2]=[N:1][C:5]([C:6]3[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][CH:11]=3)=[N:4]2)=[CH:27][CH:28]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 700424-Benzyloxybenzyl chlorideHCID 131016573-(2H-Tetrazol-5-yl)pyridin-2-amine

Product 1

HCID 24882977HCID 24882977, compoundYield 17.2%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-(2H-tetrazol-5-yl)-pyridin-2-ylamine (100 mg) described in Manufacturing Example 5-1, 4-benzyloxybenzyl chloride (172 mg), sodium iodide (111 mg), and DMF (3 mL) was added NaH (18 mg), which was stirred for 40 minutes at 60° C. Water was added to the reaction solution, which was then extracted with ethyl acetate. The organic layer was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=4:1, then 2:1, then 1:1). Ethyl acetate was added to the resulting residue, and the solids were filtered off to obtain the titled compound (38 mg).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under a reduced pressure
  3. customthe residue was purified by NH silica gel column chromatography (hexane
  4. additionEthyl acetate was added to the resulting residue
  5. filtrationthe solids were filtered off

Sources & evidence

ORD record
ord-46ec9f9b41a245e8a1886b09cdf658f3
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08183264B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes