Dimethylformamide → HCID 178505827, compound

HRID 2356625Notes

Reaction equation

HRID 2356625 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[F:26])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]#[N:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1.[N-:27]=[N+:28]=[N-:29].[Na+].[Cl-].[NH4+].CN(C)C=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[F:26])=[C:6]([CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([C:15]3[NH:29][N:28]=[N:27][N:16]=3)[N:14]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 24753222HCID 24753222, compound

Product 1

HCID 178505827HCID 178505827, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-[(5-chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)-methyl]-2-pyridinecarbonitrile (93 mg), sodium azide (51 mg), ammonium chloride (42 mg) and dimethylformamide (1 ml) was stirred at 120° for 11 hours. After cooling, water (5 ml) was added and the mixture extracted with ethyl acetate (2×5 ml). The combined extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by mass-directed autopreparation to afford the title compound (29.7 mg, 29%) as a white solid.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture extracted with ethyl acetate (2×5 ml)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by mass-directed autopreparation

Sources & evidence

ORD record
ord-324ee79d9ddd4492a0482ec89e8c01c5
Source dataset
uspto-grants-2010_07
Patent number
US07759369B2

Reaction notes

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