1-(5-Amino-1-benzofuran-2-yl)ethanone → 4-[(2-Acetyl-1-benzofuran-5-yl)amino]-2-(2-methoxyethyl)-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 729281노트

반응식

HRID 729281 반응식
Cl[C:2]1[C:3](=[O:19])[N:4]([CH2:15][CH2:16][O:17][CH3:18])[S:5](=[O:14])(=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:20][C:21]1[CH:22]=[CH:23][C:24]2[O:28][C:27]([C:29](=[O:31])[CH3:30])=[CH:26][C:25]=2[CH:32]=1>CN(C=O)C>[C:29]([C:27]1[O:28][C:24]2[CH:23]=[CH:22][C:21]([NH:20][C:2]3[C:3](=[O:19])[N:4]([CH2:15][CH2:16][O:17][CH3:18])[S:5](=[O:14])(=[O:13])[C:6]=3[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[CH:32][C:25]=2[CH:26]=1)(=[O:31])[CH3:30]

참가 물질

4

반응물 2

HCID 37833671-(5-Amino-1-benzofuran-2-yl)ethanoneHCID 672439094-Chloro-2-(2-methoxyethyl)-5-phenylisothiazol-3(2H)-one 1,1-dioxide

생성물 1

HCID 115322514-[(2-Acetyl-1-benzofuran-5-yl)amino]-2-(2-methoxyethyl)-5-phenylisothiazol-3(2H)-one 1,1-dioxide수율 34.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 4-chloro-2-(2-methoxyethyl)-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.245 g, 0.81 mmol) and 1-(5-amino-1-benzofuran-2-yl)ethanone (0.285 g, 1.63 mmol) in DMF (4 mL) was heated at 130° C. for 4 h in a microwave reactor. The product was purified by preparative HPLC [0.1M NH4OAc/MeCN, gradient A:B (8:2 to 3:7)]. The product fractions were evaporated and the residue was extracted with DCM. The organic layer was washed with saturated NaHCO3, dried through a phase separator and evaporated to give the title compound (0.123 g, 34%) as a solid; 1H NMR (500 MHz, CD3CN): δ 7.32 (ds, 1H), 7.24 (d, 1H), 7.02-7.16 (m, 7H), 3.93 (t, 2H), 3.73 (t, 2H), 3.38 (s, 3H), 2.49 (s, 3H); Mass Spectrum: M+H+ 441.

후처리

  1. customThe product was purified by preparative HPLC [0.1M NH4OAc/MeCN, gradient A:B (8:2 to 3:7)]
  2. customThe product fractions were evaporated
  3. extractionthe residue was extracted with DCM
  4. washThe organic layer was washed with saturated NaHCO3
  5. customdried through a phase separator
  6. customevaporated

출처 및 근거

ORD 기록
ord-02c27a616a494e008e2be756ba344f0d
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582629B2

반응 노트

불러오는 중…