Sodium borohydride → 6-{4-[(2-Cyclopentyl-ethylamino)-methyl]-phenoxy}-nicotinamide

HRID 130741

反応式

HRID 130741 の反応式
[CH:1]([C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=2)=[CH:5][CH:4]=1)=O.[CH:19]1([CH2:24][CH2:25][NH2:26])[CH2:23][CH2:22][CH2:21][CH2:20]1.[BH4-].[Na+]>CO>[CH:19]1([CH2:24][CH2:25][NH:26][CH2:1][C:3]2[CH:18]=[CH:17][C:6]([O:7][C:8]3[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=3)=[CH:5][CH:4]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1

参加物

5

反応物 3

HCID 4311764Sodium borohydrideHCID 53056502-CyclopentylethanamineHCID 568514226-(4-Formylphenoxy)pyridine-3-carboxamide

生成物 1

HCID 597302616-{4-[(2-Cyclopentyl-ethylamino)-methyl]-phenoxy}-nicotinamide収率 52.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Combine 6-(4-formyl-phenoxy)-nicotinamide (0.61 g, 2.54 mmol) with 2-Cyclopentyl-ethylamine (0.38 g, 3.3 mmol), 2 g of 3 {acute over (Å)} molecular sieves, and 10 mL of methanol. Stir for 18 h under nitrogen. Add sodium borohydride (0.5 g, 13.2 mmol), and stir for 24 h. Filter through Celite, remove the solvent in vacuo. Partition the residue between water (50 mL) and ethyl acetate (100 mL). Dry the organic phase (sodium sulfate), filter, and concentrate in vacuo. Adsorb on silica, and purify on an ISCO® 100 g system (eluting with 95:5:0.5 to 90:10:1 chloroform/ethanol/ammonium hydroxide) to afford 0.45 g of product. HPLC retention time: 5.93 min (98.7% purity), ESMS (M+): 340.

後処理

  1. filtrationFilter through Celite
  2. customremove the solvent in vacuo
  3. customPartition the residue between water (50 mL) and ethyl acetate (100 mL)
  4. dry with materialDry the organic phase (sodium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customAdsorb on silica, and purify on an ISCO® 100 g system (eluting with 95:5:0.5 to 90:10:1 chloroform/ethanol/ammonium hydroxide)

出典と根拠

ORDレコード
ord-84f3d6a721274a9d824451f4301ec669
出典データセット
uspto-grants-2008_06
特許番号
US07381719B2

関連ノート

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