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

HRID 130741

반응식

HRID 130741 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-84f3d6a721274a9d824451f4301ec669
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381719B2

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