Ammonium Chloride → (S)-2-Azido-4-((4-phenylbutan-2-yl)amino)nicotinonitrile

HRID 1615910Notes

Reaction equation

HRID 1615910 reaction equation
Br[C:2]1[N:9]=[CH:8][CH:7]=[C:6]([NH:10][C@H:11]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:12])[C:3]=1[C:4]#[N:5].[N-:21]=[N+:22]=[N-:23].[Na+].[Cl-].[NH4+]>CN(C=O)C>[N:21]([C:2]1[N:9]=[CH:8][CH:7]=[C:6]([NH:10][C@H:11]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:12])[C:3]=1[C:4]#[N:5])=[N+:22]=[N-:23]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 86696509(S)-2-Bromo-4-((4-phenylbutan-2-yl)amino)nicotinonitrile

Product 1

HCID 86696510(S)-2-Azido-4-((4-phenylbutan-2-yl)amino)nicotinonitrileYield 87.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared according to the methods above using (S)-2-bromo-4-((4-phenylbutan-2-yl)amino)nicotinonitrile (76.1 mg, 0.230 mmol), sodium azide (30.0 mg, 0.461 mmol) and ammonium chloride (24.65 mg, 0.461 mmol) in DMF (1.0 mL) at 100° C. for 2.5 hours to give the desired product as a yellow oil (59 mg). LC/MS (291/293, [M−H]−/[M+H]+).

Workup

  1. customPrepared
  2. customat 100° C.
  3. customfor 2.5 hours

Sources & evidence

ORD record
ord-a9643fef428a4a0fb1555aa705320215
Source dataset
uspto-grants-2014_07
Patent number
US08765767B2

Reaction notes

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