HCID 86663505, compound → HCID 56835967, compound

HRID 331705Notes

Reaction equation

HRID 331705 reaction equation
[CH2:1]([C:8]1([C:18]2[CH:19]=[C:20]([CH:34]=[CH:35][CH:36]=2)[O:21][CH2:22][CH2:23][NH:24][S:25]([C:28]2[N:29]=[CH:30][N:31]([CH3:33])[CH:32]=2)(=[O:27])=[O:26])[CH2:11][N:10]([C:12](=O)[C:13]([F:16])([F:15])[F:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1>[CH2:1]([C:8]1([C:18]2[CH:19]=[C:20]([CH:34]=[CH:35][CH:36]=2)[O:21][CH2:22][CH2:23][NH:24][S:25]([C:28]2[N:29]=[CH:30][N:31]([CH3:33])[CH:32]=2)(=[O:26])=[O:27])[CH2:11][N:10]([CH2:12][C:13]([F:16])([F:15])[F:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86663505HCID 86663505, compound

Product 1

HCID 56835967HCID 56835967, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-(2-(3-(3-benzyl-1-(2,2,2-trifluoroacetyl)azetidin-3-yl)phenoxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide (60.7 mg, 0.116 mmol) in dry tetrahydrofuran (2 ml) was added a 2M solution of borane dimethyl sulfide complex (0.290 ml, 0.581 mmol) and stirred at 60° C. for 3 h. Quenched by the dropwise addition of water and refluxed for an other 2 h, the solution was saponified with NaOH (2N) and extracted three times with dichloromethane, dried over MgSO4, filtered, evaporated and purified by flash silica gel chromatography on 4 g SiO2-cartridge using 5% MeOH in dichloromethane to afford 18.4 mg of a white solid.

Workup

  1. customQuenched by the dropwise addition of water
  2. temperaturerefluxed for an other 2 h
  3. extractionextracted three times with dichloromethane
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. custompurified by flash silica gel chromatography on 4 g SiO2-cartridge

Sources & evidence

ORD record
ord-30957a6ab02d491587498a6af78593ef
Source dataset
uspto-grants-2014_11
Patent number
US08877794B2

Reaction notes

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