Triethylamine hydrochloride → HCID 178505396, compound

HRID 417163Notes

Reaction equation

HRID 417163 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:14][NH:15][C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[C:11]3[CH:30]=[C:31]([F:35])[C:32]([F:34])=[CH:33][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.Cl.C(N(CC)CC)C.[N-:44]=[N+:45]=[N-:46].[Na+]>CC1C=CC=CC=1C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH:13]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:14][NH:15][C:16]3[CH:23]=[CH:22][C:19]([C:20]4[NH:46][N:45]=[N:44][N:21]=4)=[CH:18][CH:17]=3)[C:11]3[CH:30]=[C:31]([F:35])[C:32]([F:34])=[CH:33][C:10]=3[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochloride2×HCID 33557Sodium Azide2×HCID 66619416HCID 66619416, compound

Product 1

HCID 178505396HCID 178505396, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
145 °C

Procedure

To a suspension of 0.08 g (0.16 mmol) 4-{2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethylamino}-benzonitrile in 2 ml o-xylene were added 0.112 g (0.81 mMol) triethylamine hydrochloride and 0.053 g (0.82 mmol) sodium azide. The resulting mixture was heated to 145° C. After 72 h another 0.112 g (0.81 mMol) triethylamine hydrochloride and 0.053 g (0.82 mMol) sodium azide were added and the temperature of the oil bath was elevated to 160° C. After 24 h the oil bath was removed and the reaction mixture was poured on saturated aqueous ammonium chloride solution. The aqueous phase was extracted three times with ethyl acetate and the combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered and evaporated. The resulting light brown solid was dissolved in ethyl acetate. Upon evaporation a suspension formed which was filtered and washed with ethyl acetate. The resulting solid was taken up in 2 ml acetonitrile, heated to reflux and then cooled down to 4° C. The suspension was filtered, the solid washed with acetonitrile and dried under high vacuum. Light brown solid (25%). MS (Turbo Spray): m/z=534.2 [M+H].

Workup

  1. customwas elevated to 160° C
  2. customAfter 24 h the oil bath was removed
  3. additionthe reaction mixture was poured on saturated aqueous ammonium chloride solution
  4. extractionThe aqueous phase was extracted three times with ethyl acetate
  5. washthe combined organic layers were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. dissolutionThe resulting light brown solid was dissolved in ethyl acetate
  10. customUpon evaporation a suspension
  11. customformed which
  12. filtrationwas filtered
  13. washwashed with ethyl acetate
  14. temperatureheated
  15. temperatureto reflux
  16. temperaturecooled down to 4° C
  17. filtrationThe suspension was filtered
  18. washthe solid washed with acetonitrile
  19. customdried under high vacuum

Sources & evidence

ORD record
ord-0279af38327a46a8b162b958ea152068
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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