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

HRID 1171206ノート

反応式

HRID 1171206 の反応式
[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]

参加物

6

反応物 4

HCID 11474PiconolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 576081922-amino-N-(6-hydroxy-benzofuran-2-ylmethyl)-6-methoxymethyl-nicotinamide2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-df265b2753744edd813b216b563fe25e
出典データセット
uspto-grants-2010_11
特許番号
US07829585B2

反応ノート

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