Water → 1-[4-chloro-5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine Fumarate

HRID 1962648ノート

反応式

HRID 1962648 の反応式
[Cl:1][C:2]1[C:3]([CH:23]=[O:24])=[CH:4][N:5]([S:14]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:15])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13].[CH3:25][OH:26].[CH3:27][NH2:28].[BH4-].[Na+].[OH2:31].[O:32]1CCCC1>CO>[C:23]([OH:24])(=[O:32])/[CH:3]=[CH:4]/[C:25]([OH:31])=[O:26].[Cl:1][C:2]1[C:3]([CH2:23][NH:28][CH3:27])=[CH:4][N:5]([S:14]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:15])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13]

参加物

7

反応物 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 57454252Monomethylamine methanolHCID 866309834-chloro-5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde

生成物 1

HCID 669746331-[4-chloro-5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine Fumarate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 4-chloro-5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (429 mg) in tetrahydrofuran (5 mL) and methanol (3 mL) was added a 40% methylamine methanol solution (275 mg) at room temperature. After stirring for 30 min, sodium borohydride (99 mg) was added. After stirring at the same temperature for 1 hr, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=1:1→1:9) to give a free salt of the title compound as a yellow oil (yield 257 mg). A solution of the obtained free salt in ethyl acetate (5 mL) was added to a solution (10 mL) of fumaric acid (79 mg) in methanol, and the mixture was concentrated under reduced pressure. The residue was recrystallized from ethanol to give the title compound as colorless crystals (yield 216 mg, 36%).

後処理

  1. stirringAfter stirring at the same temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=1:1→1:9)

出典と根拠

ORDレコード
ord-7ed84b1a64e440c89b223cb3b330e3d5
出典データセット
uspto-grants-2013_04
特許番号
US08415368B2

反応ノート

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