Hydrochloric Acid → HCID 59323447, compound

HRID 2390065Notes

Reaction equation

HRID 2390065 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([CH2:12][CH2:13][NH:14][C:15](=O)[C:16]1[CH:21]=[C:20]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH:19]=[C:18]([CH2:27][CH3:28])[CH:17]=1)[CH:6]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)[CH2:5]2.Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:26][S:23]([NH:22][C:20]1[CH:21]=[C:16]([CH:17]=[C:18]([CH2:27][CH3:28])[CH:19]=1)[CH2:15][NH:14][CH2:13][CH2:12][N:7]1[CH:6]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[CH2:8]1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59323463HCID 59323463, compound

Product 1

HCID 59323447HCID 59323447, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Under an argon atmosphere, 62 mg of N-[2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethyl]-3-ethyl-5-methanesulfonylaminobenzamide was dissolved in 1 mL of THF, and a borane/THF complex (1 ml) was added thereto, followed by stirring at 60° C. overnight. The reaction liquid was cooled to room temperature, and 1 N hydrochloric acid was added thereto, followed by further stirring for 6 hours. After completion of the reaction, an aqueous sodium bicarbonate solution was added to the reaction liquid, followed by extraction with chloroform. The organic layer was then washed with an aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified using silica gel chromatography (chloroform:methanol=10:1) to obtain 42 mg (yield 70%) of a title compound as a light yellow oily substance.

Workup

  1. additiona borane/THF complex (1 ml) was added
  2. customThe reaction liquid
  3. temperaturewas cooled to room temperature
  4. stirringby further stirring for 6 hours
  5. customAfter completion of the reaction
  6. extractionfollowed by extraction with chloroform
  7. washThe organic layer was then washed with an aqueous sodium bicarbonate solution and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue obtained
  11. customwas purified

Sources & evidence

ORD record
ord-7e71666b6042440b8f67a2ba9baa197d
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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