Ammonium Chloride → 2-Azido-4-((3-phenylpropyl)amino)nicotinonitrile

HRID 1615907Notes

Reaction equation

HRID 1615907 reaction equation
Br[C:2]1[N:9]=[CH:8][CH:7]=[C:6]([NH:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]=1[C:4]#[N:5].[N-:20]=[N+:21]=[N-:22].[Na+].[Cl-].[NH4+]>CN(C=O)C>[N:20]([C:2]1[N:9]=[CH:8][CH:7]=[C:6]([NH:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]=1[C:4]#[N:5])=[N+:21]=[N-:22]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 866965062-Bromo-4-((3-phenylpropyl)amino)nicotinonitrile

Product 1

HCID 866965072-Azido-4-((3-phenylpropyl)amino)nicotinonitrileYield 91.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to the methods above using 2-bromo-4-((3-phenylpropyl)amino)nicotinonitrile (43.6 mg, 0.138 mmol), sodium azide (17.93 mg, 0.276 mmol) and ammonium chloride (14.75 mg, 0.276 mmol) in DMF (0.5 mL) at 100° C. for 18 hours to give the desired product as a yellow oil (35 mg). LC/MS (277, [M−H]−). This material was used as is.

Workup

  1. customPrepared
  2. customat 100° C.
  3. customfor 18 hours

Sources & evidence

ORD record
ord-e068fc80cce74db9a8380a072880a662
Source dataset
uspto-grants-2014_07
Patent number
US08765767B2

Reaction notes

Loading…