Ammonium Chloride → HCID 178496774, compound

HRID 2409452Notes

Reaction equation

HRID 2409452 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:13]2[CH:14]=[C:15]([CH2:18][C:19]#[N:20])[CH:16]=[CH:17][C:12]=2[C:11]2[NH:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]1=[O:21].[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-].[NH4+]>CN(C)C=O>[NH:22]1[C:19]([CH2:18][C:15]2[CH:16]=[CH:17][C:12]3[C:11]4[NH:10][CH2:9][CH2:8][CH2:7][C:6]=4[C:5](=[O:21])[N:4]([CH2:3][O:2][CH3:1])[C:13]=3[CH:14]=2)=[N:20][N:24]=[N:23]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 58424882HCID 58424882, compound

Product 1

HCID 178496774HCID 178496774, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (65 mg, 0.23 mmol) prepared in step 1 was dissolved in N,N-dimethylformamide (5 ml), sequentially added with sodium azide (75 mg, 1.15 mmol) and ammonium chloride (61 mg, 1.15 mmol). The resulting mixture was refluxed for 48 hours and cooled to room temperature. The mixture was washed with chloroform and the water layer was concentrated to dryness. The residue was then washend with methanol and filtered. The filtrate was purified by flash column chromatography (chloroform:methanol=5:1) to obtain the title compound (34 mg, yield: 45%, yellow solid).

Workup

  1. temperatureThe resulting mixture was refluxed for 48 hours
  2. washThe mixture was washed with chloroform
  3. concentrationthe water layer was concentrated to dryness
  4. filtrationfiltered
  5. customThe filtrate was purified by flash column chromatography (chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-21d9f0d310c149158fb68f4a1e1bb2ae
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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