Trifluoroacetic acid → 2-amino-N-(6-hydroxy-benzofuran-2-ylmethyl)-6-methoxymethyl-nicotinamide

HRID 1171198ノート

反応式

HRID 1171198 の反応式
FC(F)(F)C(O)=O.[NH2:8][C:9]1[N:35]=[C:34]([CH2:36][O:37][CH3:38])[CH:33]=[CH:32][C:10]=1[C:11]([NH:13][CH2:14][C:15]1[O:16][C:17]2[CH:23]=[C:22]([O:24]CC3C=CC=CC=3)[CH:21]=[CH:20][C:18]=2[CH:19]=1)=[O:12].C1(SC)C=CC=CC=1.C(=O)(O)[O-].[Na+]>O>[NH2:8][C:9]1[N:35]=[C:34]([CH2:36][O:37][CH3:38])[CH:33]=[CH:32][C:10]=1[C:11]([NH:13][CH2:14][C:15]1[O:16][C:17]2[CH:23]=[C:22]([OH:24])[CH:21]=[CH:20][C:18]=2[CH:19]=1)=[O:12]

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 516892Sodium BicarbonateHCID 119607292-Amino-N-(6-benzyloxy-benzofuran-2-ylmethyl)-6-methoxymethyl-nicotinamide

生成物 1

HCID 576081922-amino-N-(6-hydroxy-benzofuran-2-ylmethyl)-6-methoxymethyl-nicotinamide収率 76%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

To a trifluoroacetic acid (11 mL) solution of 2-amino-N-(6-benzyloxy-benzofuran-2-ylmethyl)-6-methoxymethyl-nicotinamide (557 mg, 1.33 mmol) described in Example 4 was added thioanisole (626 μL, 5.35 mmol) at 0° C., which was stirred at 0° C. for 3 hours. To the reaction solution were added sodium bicarbonate and water at 0° C. followed by extraction with ethyl acetate and tetrahydrofuran. The organic layer was washed with sat. NaCl followed by drying over anhydrous magnesium sulfate and filtering. The filtrate was concentrated under a reduced pressure and the residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=10:1) to obtain the title compound (331 mg, 76%) as a white solid.

後処理

  1. extractionfollowed by extraction with ethyl acetate and tetrahydrofuran
  2. washThe organic layer was washed with sat. NaCl
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. customthe residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=10:1)

出典と根拠

ORDレコード
ord-d6f799def7f044c192d429ccdc3b7c23
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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