Methanol → 6-(4-benzyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)-N-cyclopentyl-N-(3-hydroxypropyl)pyridine-3-sulfonamide

HRID 45252ノート

反応式

HRID 45252 の反応式
[CH2:1]([C:8]1[C:12](=[O:13])[N:11]([C:14]2[N:19]=[CH:18][C:17]([S:20]([N:23]([CH2:29][CH2:30][CH2:31][O:32]CC3C=CC=CC=3)[CH:24]3[CH2:28][CH2:27][CH2:26][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.CO>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]([CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:29][CH2:30][CH2:31][OH:32])(=[O:21])=[O:22])=[CH:16][CH:15]=2)[NH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 887MethanolHCID 25134Boron tribromideHCID 674548866-(4-benzyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)-N-[3-(benzyloxy)propyl]-N-cyclopentylpyridine-3-sulfonamide

生成物 1

HCID 674558336-(4-benzyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)-N-cyclopentyl-N-(3-hydroxypropyl)pyridine-3-sulfonamide収率 86%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 150 mg (0.27 mmol) of 6-(4-benzyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)-N-[3-(benzyloxy)propyl]-N-cyclopentylpyridine-3-sulfonamide in 2 mL of DCM is added dropwise, at −78° C. under argon, 0.82 mL (0.82 mmol) of boron tribromide (1M in DCM). Stirring is continued for 1 hour at −78° C., and 2 mL of MeOH are then added at 0° C. The medium is taken up in 40 mL of DCM, washed successively with saturated NaHCO3 solution (30 mL) and brine (30 mL), dried over Na2SO4 and then concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a 9/1 DCM/MeOH mixture. 106 mg of 6-(4-benzyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)-N-cyclopentyl-N-(3-hydroxypropyl)pyridine-3-sulfonamide are thus obtained in the form of a powder.

後処理

  1. washwashed successively with saturated NaHCO3 solution (30 mL) and brine (30 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. custompurified by chromatography on a column of silica gel
  5. washeluting with a 9/1 DCM/MeOH mixture

出典と根拠

ORDレコード
ord-524d5b8a89904105974cb1f5b6ff1260
出典データセット
uspto-grants-2013_09
特許番号
US08541455B2

反応ノート

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