Ammonium Chloride → HCID 57832734, compound

HRID 729454Notes

Reaction equation

HRID 729454 reaction equation
[Br:1][C:2]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:12]=[CH:13][C:14]([C:17]#[N:18])=[N:15][CH:16]=2)[CH2:7][CH2:6]1.[N-:24]=[N+:25]=[N-:26].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[N:15][C:14]([C:17]3[N:24]=[N:25][NH:26][N:18]=3)=[CH:13][N:12]=2)[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68819220HCID 68819220, compound

Product 1

HCID 57832734HCID 57832734, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyrazine-2-carbonitrile from Step 5 (0.200 g, 0.530 mmol) in DMF (2 mL) was added sodium azide (0.070 g, 1.06 mmol) and ammonium chloride (0.284 g, 5.30 mmol). After a period of 3 h at 130° C., the reaction mixture was cooled and partitioned between ethyl acetate and brine. The organic phase was separated, dried over sodium sulfate and evaporated. To the crude product was added a mixture of ether-hexane (1:1). The resulting solid was filtered to provide the title compound.

Workup

  1. temperaturethe reaction mixture was cooled
  2. custompartitioned between ethyl acetate and brine
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. additionTo the crude product was added
  7. additiona mixture of ether-hexane (1:1)
  8. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-a359bc09b15043a59a73a17b106b7778
Source dataset
uspto-grants-2009_09
Patent number
US07582633B2

Reaction notes

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