Ammonium Chloride → HCID 178428440, compound

HRID 1932394Notes

Reaction equation

HRID 1932394 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl:5][C:6]1[CH:7]=[C:8]([CH:33]=[CH:34][CH:35]=1)[CH2:9][N:10]1[C:14]2=[C:15]([N:21]3[CH2:30][CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22]3)[N:16]=[C:17]([C:19]#[N:20])[CH:18]=[C:13]2[C:12]([CH3:31])=[C:11]1[CH3:32].[Cl-].[NH4+].N([O-])=O.[Na+]>CN(C)C=O>[Cl:5][C:6]1[CH:7]=[C:8]([CH:33]=[CH:34][CH:35]=1)[CH2:9][N:10]1[C:14]2=[C:15]([N:21]3[CH2:30][CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:22]3)[N:16]=[C:17]([C:19]3[NH:20][N:3]=[N:2][N:1]=3)[CH:18]=[C:13]2[C:12]([CH3:31])=[C:11]1[CH3:32]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 67141952HCID 67141952, compound

Product 1

HCID 178428440HCID 178428440, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (137 mg, 2.1 mmol) was added at 0° C. to a solution of 1-(3-chlorobenzyl)-7-(3,4-dihydro-1H-isoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-carbonitrile (300 mg, 0.7 mmol) prepared in Example 689 and ammonium chloride (74.9 mg, 1.4 mmol) in anhydrous N,N-dimethylformamide (10 ml). The reaction mixture was refluxed overnight. 6% sodium nitrite solution was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3, v/v) to give 110 mg of the titled compound as a white solid. (Yield: 33%).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3

Sources & evidence

ORD record
ord-e88e1ca598594a06a281fefc855e974d
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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