Hydrochloric Acid → HCID 18412656, compound

HRID 992647Notes

Reaction equation

HRID 992647 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:8]([C:10]1[CH:21]=[CH:20][C:13]2[N:14]([CH3:19])[C:15]([CH2:17][NH2:18])=[N:16][C:12]=2[CH:11]=1)=[O:9].FC(F)(F)C([O-])=O.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:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:8]([C:10]1[CH:21]=[CH:20][C:13]2[N:14]([CH3:19])[C:15]([CH2:17][NH:18][C:46]3[N:47]=[CH:48][C:49]([C:52]#[N:53])=[CH:50][CH:51]=3)=[N:16][C:12]=2[CH:11]=1)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 131721872HCID 131721872, compound

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-aminomethyl-benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)-amide-trifluoracetate were stirred into 10 ml of N-ethyl-diisopropylamine and heated to 100° C. for 15 minutes. After the addition of 720 mg (5.25 mmol) of 2-chloro-5-cyano-pyridine 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 sulphate. 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. temperaturewas 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 sulphate
  6. customAfter evaporation of the solvent the crude product
  7. customwas 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-6bf4e0c1777240ff9c0ae111bdbab7d9
Source dataset
uspto-grants-2002_10
Patent number
US06469039B1

Reaction notes

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