Sodium Azide → HCID 178517237, compound

HRID 2182624Notes

Reaction equation

HRID 2182624 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([C:7]1[CH:31]=[CH:30][C:10]([CH2:11][C:12]23[CH2:19][CH2:18][CH2:17][N:16]2[C:15](=[O:20])[N:14]([C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)[C:13]3=[O:29])=[CH:9][CH:8]=1)#[N:6]>CN(C=O)C>[NH:1]1[C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][C:12]34[CH2:19][CH2:18][CH2:17][N:16]3[C:15](=[O:20])[N:14]([C:21]3[CH:22]=[C:23]([Cl:28])[CH:24]=[C:25]([Cl:27])[CH:26]=3)[C:13]4=[O:29])=[CH:30][CH:31]=2)=[N:6][N:3]=[N:2]1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 22479221HCID 22479221, compound

Product 1

HCID 178517237HCID 178517237, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

NaN3 (64.5 mg) was added to a solution of Example 21 (137 mg) in DMF (3 mL). The reaction mixture was sealed and heated at 140° C. for 72 hours. The reaction mixture was cooled to room temperature and the solvent removed under reduced pressure. The residue was purified by HPLC (18C-Waters 40×210 mm, 1% HOAc/CH3CN gradient) to provide the titled compound (27 mg). MS (m/z) 457 (MH+). mp. 194.8° C.

Workup

  1. customThe reaction mixture was sealed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe solvent removed under reduced pressure
  4. customThe residue was purified by HPLC (18C-Waters 40×210 mm, 1% HOAc/CH3CN gradient)

Sources & evidence

ORD record
ord-8efbbae9199a4eeeb27cd6c8e4b6de4d
Source dataset
uspto-grants-2005_05
Patent number
US06897225B1

Reaction notes

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