Hydrochloric Acid → HCID 18412656, compound

HRID 2227677Notes

Reaction equation

HRID 2227677 reaction equation
FC(F)(F)C(O)=O.[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:15]([C:17]1[CH:28]=[CH:27][C:20]2[N:21]([CH3:26])[C:22]([CH2:24][NH2:25])=[N:23][C:19]=2[CH:18]=1)=[O:16].C(N(C(C)C)C(C)C)C.Cl[C:46]1[CH:51]=[CH:50][C:49]([C:52]#[N:53])=[CH:48][N:47]=1.Cl>O>[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:15]([C:17]1[CH:28]=[CH:27][C:20]2[N:21]([CH3:26])[C:22]([CH2:24][NH:25][C:46]3[N:47]=[CH:48][C:49]([C:52]#[N:53])=[CH:50][CH:51]=3)=[N:23][C:19]=2[CH:18]=1)=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 184124831-Methyl-2-aminomethylbenzimidazol-5-yl-carboxylic acid-n-(2-pyridyl)-n-(2-ethoxycarbonylethyl)amide trifluoroacetate

Product 1

HCID 18412656HCID 18412656, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

1.5 g (3.25 mmol) of 1-methyl-2-aminomethylbenzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide trifluoroacetate were stirred into 10 ml of N-ethyldiisopropylamine and heated to 100° C. for 15 minutes. After the addition of 720 mg (5.25 mmol) of 2-chloro-5-cyanopyridine, the reaction mixture was heated to 125° C. for 2 hours. After cooling to ambient temperature and stirring with about 20 ml of water, the pH was adjusted to 4 by the addition of 1N hydrochloric acid and the mixture was extracted 3 times with ethyl acetate. The combined organic phases were washed with saline solution and dried over sodium sulfate. After evaporation of the solvent, the crude product was chromatographed on silica gel, eluting first with methylene chloride, later with methylene chloride/ethanol (25:1) and (19:1). The desired fractions were combined and evaporated down.

Workup

  1. temperaturethe reaction mixture was heated to 125° C. for 2 hours
  2. temperatureAfter cooling to ambient temperature
  3. extractionthe mixture was extracted 3 times with ethyl acetate
  4. washThe combined organic phases were washed with saline solution
  5. dry with materialdried over sodium sulfate
  6. customAfter evaporation of the solvent
  7. customthe crude product was chromatographed on silica gel
  8. washeluting first with methylene chloride, later with methylene chloride/ethanol (25:1) and (19:1)
  9. customevaporated down

Sources & evidence

ORD record
ord-0631a66615a24709aa382f6259864c2c
Source dataset
uspto-grants-2002_07
Patent number
US06414008B1

Reaction notes

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