Methanol → HCID 86659755, compound

HRID 45259Notes

Reaction equation

HRID 45259 reaction equation
[CH2:1]([C:8]1[C:12](=[O:13])[N:11]([C:14]2[N:19]=[CH:18][C:17]([S:20]([NH:23][C@@H:24]3[CH2:28][CH2:27][C@H:26]([CH2:29][O:30]CC4C=CC=CC=4)[CH2:25]3)(=[O:22])=[O:21])=[CH:16][CH:15]=2)[NH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.[CH3:42]O>C(Cl)Cl>[CH2:1]([C:8]1[C:12](=[O:13])[N:11]([C:14]2[N:19]=[CH:18][C:17]([S:20]([N:23]([C@@H:24]3[CH2:28][CH2:27][C@H:26]([CH2:29][OH:30])[CH2:25]3)[CH3:42])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[NH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 67454999HCID 67454999, compound

Product 1

HCID 86659755HCID 86659755, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.3 g (0.57 mmol) of 6-(4-benzyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)-N-{(1R,3S)-3-[(benzyloxy)methyl]cyclopentyl}pyridine-3-sulfonamide in 2 mL of DCM cooled to −78° C. are added 1.7 mL of boron tribromide. The temperature is then allowed to rise to 0° C. and stirring is continued for 1 hour at 0° C. 10 mL of MeOH are then added at −10° C. and the medium is concentrated under reduced pressure. The medium is taken up in 100 mL of DCM, washed successively with saturated NaHCO3 solution (2×20 mL) and brine (20 mL), dried over Na2SO4, concentrated under reduced pressure and then purified by chromatography on a column of silica gel, eluting with a 90/10 DCM/MeOH mixture. 126 mg of 6-(4-benzyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)-N-[(1R,3S)-3-(hydroxymethyl)cyclopentyl]-N-methylpyridine-3-sulfonamide are obtained in the form of a powder.

Workup

  1. customto rise to 0° C.
  2. concentrationthe medium is concentrated under reduced pressure
  3. washwashed successively with saturated NaHCO3 solution (2×20 mL) and brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. custompurified by chromatography on a column of silica gel
  7. washeluting with a 90/10 DCM/MeOH mixture

Sources & evidence

ORD record
ord-12ddb6a7a15048fca5597ed14a63d538
Source dataset
uspto-grants-2013_09
Patent number
US08541455B2

Reaction notes

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