Piconol → 2-Amino-6-methoxymethyl-N-(6-(pyridin-2-ylmethoxy)-benzofuran-2-ylmethyl)-nicotinamide

HRID 1171206노트

반응식

HRID 1171206 반응식
[NH2:1][C:2]1[N:21]=[C:20]([CH2:22][O:23][CH3:24])[CH:19]=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[O:9][C:10]2[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:11]=2[CH:12]=1)=[O:5].O[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[NH2:1][C:2]1[N:21]=[C:20]([CH2:22][O:23][CH3:24])[CH:19]=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[O:9][C:10]2[CH:16]=[C:15]([O:17][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[CH:14]=[CH:13][C:11]=2[CH:12]=1)=[O:5]

참가 물질

6

반응물 4

HCID 11474PiconolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 576081922-amino-N-(6-hydroxy-benzofuran-2-ylmethyl)-6-methoxymethyl-nicotinamide2회

생성물 1

HCID 576082702-Amino-6-methoxymethyl-N-(6-(pyridin-2-ylmethoxy)-benzofuran-2-ylmethyl)-nicotinamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a tetrahydrofuran (2 mL) solution of 2-amino-N-(6-hydroxy-benzofuran-2-ylmethyl)-6-methoxymethyl-nicotinamide (20 mg, 61 μmol) described in Production Example 5-1 were added 2-(hydroxymethyl)pyridine (6.5 μL, 67 μmol), triphenylphosphine (19.2 mg, 73 μmol) and diethylazodicarboxylate (33 μL, 73 μmol) at room temperature, which was stirred at room temperature for 30 minutes. After filtering the reaction solution, the filtrate was purified by reverse phase high-performance liquid chromatography (using an acetonitrile-aqueous mobile phase (containing 0.1% trifluoroacetic acid)) to obtain a mixture of the title compound and 2-amino-N-(6-hydroxy-benzofuran-2-ylmethyl)-6-methoxymethyl-nicotinamide. Then, this mixture was purified by silica gel column chromatography (ethyl acetate:methanol=10:1) to obtain the title compound (6 mg, 24%) as a white solid.

후처리

  1. filtrationAfter filtering the reaction solution
  2. customthe filtrate was purified by reverse phase high-performance liquid chromatography (
  3. additionan acetonitrile-aqueous mobile phase (containing 0.1% trifluoroacetic acid))
  4. customto obtain

출처 및 근거

ORD 기록
ord-df265b2753744edd813b216b563fe25e
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829585B2

반응 노트

불러오는 중…