Hydrochloric Acid → HCID 178521901, compound

HRID 1161356Notes

Reaction equation

HRID 1161356 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=3)=[O:15])[C:11]3[CH:31]=[C:32]([F:36])[C:33]([F:35])=[CH:34][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.Cl.C([NH+](CC)CC)C.[N-:45]=[N+:46]=[N-:47].[Na+].Cl>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]4[NH:47][N:46]=[N:45][N:24]=4)=[CH:21][CH:22]=3)=[O:15])[C:11]3[CH:31]=[C:32]([F:36])[C:33]([F:35])=[CH:34][C:10]=3[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 21900368Triethylammonium hydrochlorideHCID 68645726HCID 68645726, compound

Product 1

HCID 178521901HCID 178521901, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
145 °C

Procedure

The suspension of 0.13 g (0.25 mmol) 2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-N-(4-cyano-phenyl)-2-cyclohexyl-acetamide, 0.17 g (1.26 mmol) triethylammonium hydrochloride and 82 mg (1.26 mmol) sodium azide in 3 mL ortho-xylene was stirred at 145° C. for 2.5 hrs. The brown suspension was poured on 1M aqueous hydrochloric acid solution and extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and evaporated to dryness. The residue was dissolved in acetonitrile and a few drops of water were added upon which precipitation started. The formed suspension was filtered and the solid was washed with acetonitrile containing a few drops of water to give the desired compound as a white solid (68%). MS (ES+): 548.3 (M+H).

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in acetonitrile
  6. additiona few drops of water were added upon which precipitation
  7. filtrationThe formed suspension was filtered
  8. washthe solid was washed with acetonitrile containing a few drops of water

Sources & evidence

ORD record
ord-12d3767d84ce4be6b9d0e229cee80709
Source dataset
uspto-grants-2010_10
Patent number
US07816540B2

Reaction notes

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