Sodium Azide → HCID 24882976, compound

HRID 1927216Notes

Reaction equation

HRID 1927216 reaction equation
[C:1]([C:3]1[C:4]([NH2:10])=[N:5][C:6]([NH2:9])=[CH:7][CH:8]=1)#[CH:2].[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25]Cl)=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[N-:27]=[N+:28]=[N-:29].[Na+].C(=O)(O)[O-].[Na+]>S([O-])([O-])(=O)=O.[Cu+2].[Cu].O.CN1C(=O)CCC1>[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:27]2[CH:2]=[C:1]([C:3]3[C:4]([NH2:10])=[N:5][C:6]([NH2:9])=[CH:7][CH:8]=3)[N:29]=[N:28]2)=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

9

Reactant 4

HCID 33557Sodium AzideHCID 700424-Benzyloxybenzyl chlorideHCID 516892Sodium BicarbonateHCID 552816763-Ethynylpyridine-2,6-diamine

Product 1

HCID 24882976HCID 24882976, compoundYield 2.1%

Reagents, catalysts & solvents 4

HCID 23978CopperCatalystHCID 24462Copper SulfateCatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of NMP (200 μL) and water (200 μL) of 3-ethynyl-pyridin-2,6-diamine (20 mg) described in Manufacturing Example 4-3 were added 1-benzyloxy-4-chloromethyl-benzene (37 mg), sodium azide (15 mg), copper sulfate (4.8 mg), and copper (7.4 mg) at room temperature, and this mixture was irradiated for 30 seconds at no higher than 125° C. with 100 W microwaves. Aqueous sodium bicarbonate was added to the reaction mixture, which was extracted with ethyl acetate. The solvent was evaporated from the organic layer under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:3, then with ethyl acetate) to obtain the titled compound (1.2 mg).

Workup

  1. customthis mixture was irradiated for 30 seconds at no higher than 125° C. with 100 W microwaves
  2. extractionwas extracted with ethyl acetate
  3. customThe solvent was evaporated from the organic layer under a reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (heptane

Sources & evidence

ORD record
ord-44713a821f7842a6bdb6182db12ad534
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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