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

HRID 1171198노트

반응식

HRID 1171198 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d6f799def7f044c192d429ccdc3b7c23
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829585B2

반응 노트

불러오는 중…