Water → HCID 86612284, compound

HRID 2402282Notes

Reaction equation

HRID 2402282 reaction equation
[CH2:1]([N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[CH2:18][CH2:19]C(NC1SC=CN=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:28]=[N+:29]=[N-:30].[Na+].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[N:28]([CH2:19][CH2:18][CH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16](=[O:17])[N:8]1[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[N+:29]=[N-:30]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 58869823HCID 58869823, compound

Product 1

HCID 86612284HCID 86612284, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 1, Part B (2.0 g, 7.5 mmol), sodium azide (731 mg, 11.25 mmol), and K2CO3 (3.1 g, 225 mmol) were stirred in 20 mL DMF at 50° C. for 16 h. The mixture was poured into water and washed with EtOAc. The organic phase was washed with water and brine, then dried (Na2SO4), filtered and evaporated. The title compound was purified by silica gel chromatography (2.04 g, 93%).

Workup

  1. washwashed with EtOAc
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe title compound was purified by silica gel chromatography (2.04 g, 93%)

Sources & evidence

ORD record
ord-ca49fedc993643ad996e7f7999a0a716
Source dataset
uspto-grants-2014_08
Patent number
US08796313B2

Reaction notes

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