Hydrochloric Acid → HCID 178488854, compound

HRID 417127Notes

Reaction equation

HRID 417127 reaction equation
[CH:1]1([CH:7]([N:20]2[C:24]3[CH:25]=[C:26]([F:30])[C:27]([F:29])=[CH:28][C:23]=3[N:22]=[C:21]2[C:31]2[C:32]([O:39][CH3:40])=[N:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=2)[CH2:8][O:9][C:10]2[C:17]([CH3:18])=[CH:16][C:13]([C:14]#[N:15])=[CH:12][C:11]=2[CH3:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C(N(CC)CC)C.[N-:49]=[N+:50]=[N-:51].[Na+].Cl>CC1C=CC=CC=1C>[CH:1]1([CH:7]([N:20]2[C:24]3[CH:25]=[C:26]([F:30])[C:27]([F:29])=[CH:28][C:23]=3[N:22]=[C:21]2[C:31]2[C:32]([O:39][CH3:40])=[N:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=2)[CH2:8][O:9][C:10]2[C:11]([CH3:19])=[CH:12][C:13]([C:14]3[NH:51][N:50]=[N:49][N:15]=3)=[CH:16][C:17]=2[CH3:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 66619332HCID 66619332, compound

Product 1

HCID 178488854HCID 178488854, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
145 °C

Procedure

To a solution of 0.18 g (0.33 mmol) 4-{2-cyclohexyl-2-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-ethoxy}-3,5-dimethyl-benzonitrile in 3 ml o-xylene were added 0.227 g (1.65 mmol) triethylamine hydrochloride and 0.107 g (2.65 mMol) sodium azide and the solution was heated for 7 h at 145° C. (oil bath temperature). The reaction was allowed to cool down to room temperature overnight and then was poured onto 1M aqueous hydrochloric acid solution and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The remaining oil was dissolved in acetonitrile, the solution was completely evaporated and the residue dissolved in 20 ml tert-butyl methyl ether under warming to 45° C. The solution was partially evaporated, then stored at 4° C. overnight. The resulting suspension was filtered, washed with tert-butyl methyl ether and dried under high vacuum. Light brown solid (75%). MS (Turbo Spray): m/z=590.44 [M+H].

Workup

  1. temperatureto cool down to room temperature overnight
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe remaining oil was dissolved in acetonitrile
  8. customthe solution was completely evaporated
  9. dissolutionthe residue dissolved in 20 ml tert-butyl methyl ether
  10. temperatureunder warming to 45° C
  11. customThe solution was partially evaporated
  12. filtrationThe resulting suspension was filtered
  13. washwashed with tert-butyl methyl ether
  14. customdried under high vacuum

Sources & evidence

ORD record
ord-29acca5615014e35a920719deee8a17f
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

Loading…