HCID 59323414, compound → HCID 59323083, compound

HRID 2390063Notes

Reaction equation

HRID 2390063 reaction equation
C(OC([N:11]([CH2:33][C:34]1[CH:39]=[C:38]([NH:40][S:41]([CH3:44])(=[O:43])=[O:42])[CH:37]=[C:36]([NH:45][S:46]([CH3:49])(=[O:48])=[O:47])[CH:35]=1)[CH2:12][CH2:13][N:14]1[CH:23]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([F:32])[CH:20]=2)[CH2:15]1)=O)C1C=CC=CC=1>CO.[Pd]>[CH3:44][S:41]([NH:40][C:38]1[CH:39]=[C:34]([CH:35]=[C:36]([NH:45][S:46]([CH3:49])(=[O:47])=[O:48])[CH:37]=1)[CH2:33][NH:11][CH2:12][CH2:13][N:14]1[CH:23]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([F:32])[CH:20]=2)[CH2:15]1)(=[O:42])=[O:43]

Participants

4

Reactant 1

HCID 59323414HCID 59323414, compound

Product 1

HCID 59323083HCID 59323083, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-(benzyloxycarbonyl)-N-[3,5-bis(methanesulfonyl)aminobenzyl]-2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine (25.0 mg, 0.04 mmol) was dissolved in 1.5 mL of methanol, and 100 mg of Pd—C was added thereto at room temperature, followed by stirring for 1.5 hours under a hydrogen gas atmosphere. After completion of the reaction, the reaction liquid was filtered through Celite. The filtrate was concentrated under reduced pressure, and the solvent was removed by evaporation and purified by PLC to obtain 6.8 mg (yield 33%) of a desired product as a pale yellow oily substance.

Workup

  1. customat room temperature
  2. customAfter completion of the reaction
  3. customthe reaction liquid
  4. filtrationwas filtered through Celite
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe solvent was removed by evaporation
  7. custompurified by PLC

Sources & evidence

ORD record
ord-9bede2c15bef48d190c2712887524852
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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