Ammonium Chloride → HCID 178505489, compound

HRID 729484Notes

Reaction equation

HRID 729484 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:3]=1[O:4][CH:5]1[CH2:8][N:7]([C:9]2[N:10]=[CH:11][C:12]([C:15]#[N:16])=[N:13][CH:14]=2)[CH2:6]1.[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:3]=1[O:4][CH:5]1[CH2:8][N:7]([C:9]2[CH:14]=[N:13][C:12]([C:15]3[NH:24][N:23]=[N:22][N:16]=3)=[CH:11][N:10]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68818057HCID 68818057, compound

Product 1

HCID 178505489HCID 178505489, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5-[3-(2-bromo-5-fluorophenoxy)azetidin-1-yl]pyrazine-2-carbonitrile (0.48 g, 1.36 mmol), sodium azide (0.18 g, 2.7 mmol), and ammonium chloride (0.73 g, 1.36 mmol) in DMF (4 mL) was heated at 130° C. After a period of 4 h, the reaction mixture was partitioned between ethyl acetate and saturated ammonium chloride. The resulting solid was filtered and washed with water and ether. The solid was taken up in toluene and the solvent evaporated to provide the desired product.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and saturated ammonium chloride
  2. filtrationThe resulting solid was filtered
  3. washwashed with water and ether
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-2bf508acf47749e1bc128429e009d6c5
Source dataset
uspto-grants-2009_09
Patent number
US07582633B2

Reaction notes

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