Sodium Azide → HCID 58972934, compound

HRID 1171059Notes

Reaction equation

HRID 1171059 reaction equation
[C:1]([O:5][C:6]([N:8]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH2:19]Br)[CH:17]=2)[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:28]=[N+:29]=[N-:30].[Na+]>CS(C)=O.O>[C:1]([O:5][C:6]([N:8]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH2:19][N:28]=[N+:29]=[N-:30])[CH:17]=2)[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 58972993HCID 58972993, compound

Product 1

HCID 58972934HCID 58972934, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of bis-tert-butoxycarbonyl-(7-bromomethyl-isoquinolin-1-yl)amine (280 mg, 0.64 mmol) and NaN3 (300 mg, 4.6 mmol) in 3 mL of DMSO was heated at 85° C. for 1 h. Then the solution was cooled down to rt, diluted with water and extracted with 50% EtOAc in hexane. The combined organic layers were washed with water. Removal of solvents furnished the crude product as a yellow oil (200 mg).

Workup

  1. temperatureThen the solution was cooled down to rt
  2. extractionextracted with 50% EtOAc in hexane
  3. washThe combined organic layers were washed with water
  4. customRemoval of solvents

Sources & evidence

ORD record
ord-4ca1abaade1240b58aab95680cbc3adb
Source dataset
uspto-grants-2010_11
Patent number
US07829584B2

Reaction notes

Loading…