Dimethylformamide → HCID 24883026, compound

HRID 1927245Notes

Reaction equation

HRID 1927245 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]2[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][CH:11]=2)=[N:2]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.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:25][N:1]2[CH:5]=[N:4][C:3]([C:6]3[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][CH:11]=3)=[N:2]2)=[CH:27][CH:28]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 700424-Benzyloxybenzyl chlorideHCID 178508378HCID 178508378, compound

Product 1

HCID 24883026HCID 24883026, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

3-(1H-[1,2,4]triazol-3-yl)-pyridin-2-ylamine (20 mg) described in Manufacturing Example 14-3, 4-benzyloxybenzyl chloride (32 mg), potassium carbonate (86 mg, and DMF (3.0 mL) were stirred for 0.5 hour at 60° C. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic layer was concentrated and purified by NH silica gel column chromatography (heptane:ethyl acetate=2:1, then 1:1) to obtain the titled compound (27 mg).

Workup

  1. extractionwas extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. custompurified by NH silica gel column chromatography (heptane

Sources & evidence

ORD record
ord-695a234e5d3c4c4fbbffcfdd7ab41514
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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