Sodium Bicarbonate → 1-(5-Hydroxy-6,7-dimethyl-benzofuran-2-yl)-2-morpholin-4-yl-ethanone

HRID 480981노트

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HRID 480981 반응식
[CH3:1][C:2]1[C:19]([O:20]C(=O)C)=[CH:18][C:5]2[CH:6]=[C:7]([C:9](=[O:17])[CH2:10][N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[O:8][C:4]=2[C:3]=1[CH3:24].C(=O)(O)[O-].[Na+]>CO>[OH:20][C:19]1[C:2]([CH3:1])=[C:3]([CH3:24])[C:4]2[O:8][C:7]([C:9](=[O:17])[CH2:10][N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:6][C:5]=2[CH:18]=1

참가 물질

4

반응물 2

HCID 516892Sodium BicarbonateHCID 10236780Acetic acid 6,7-dimethyl-2-(2-morpholin-4-yl-acetyl)-benzofuran-5-yl ester

생성물 1

HCID 102364101-(5-Hydroxy-6,7-dimethyl-benzofuran-2-yl)-2-morpholin-4-yl-ethanone수율 54.8%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of acetic acid 6,7-dimethyl-2-(2-morpholin4-yl-acetyl)-benzofuran-5-yl ester (23 mg), prepared as in Example 17, in MeOH (10 mL) was stirred while sodium bicarbonate (10 mg) was added. Then the mixture was stirred at RT overnight, followed by evaporation to dryness. The residue was purified by silica gel column, eluting with 5% MeOH in dichloromethane to give 11 mg of 1-(5-hydroxy-6,7-dimethyl-benzofuran-2-yl)-2-morpholin-4-yl-ethanone as an oil. Conversion into HCl salt gave a yellow solid. 1H NMR (CD3OD, 300 MHz) δ: 7.60 (s, 1H), 7.20 (s, 1H), 3.78 (m, 6H), 2.64 (m, 4H), 2.50 (s, 3H), 2.40 (s, 3H) ppm. 13C NMR (CDCl3, 75 MHz) δ: 187.98, 170.20, 153.31, 152.29, 146.58, 130.44, 124.53, 122.80, 114.36, 113.15, 64.69, 53.79, 21.28, 13.47, 12.86 ppm. M/S 290 (M+H+).

후처리

  1. additionwas added
  2. customfollowed by evaporation to dryness
  3. customThe residue was purified by silica gel column
  4. washeluting with 5% MeOH in dichloromethane

출처 및 근거

ORD 기록
ord-0342f01a9fa946ce88315252eda02b97
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06653346B1

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