Triethylamine → 5-bromo-N2-methoxy-N2,N3-dimethyl-6-(N-methylmethylsulfonamido)benzofuran-2,3-dicarboxamide

HRID 595664노트

반응식

HRID 595664 반응식
[Br:1][C:2]1[C:3]([N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])=[CH:4][C:5]2[O:9][C:8]([C:10]([OH:12])=O)=[C:7]([C:13](=[O:16])[NH:14][CH3:15])[C:6]=2[CH:17]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN(CC)CC.Cl.[CH3:53][NH:54][O:55][CH3:56]>CN(C=O)C>[Br:1][C:2]1[C:3]([N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])=[CH:4][C:5]2[O:9][C:8]([C:10]([N:54]([O:55][CH3:56])[CH3:53])=[O:12])=[C:7]([C:13]([NH:14][CH3:15])=[O:16])[C:6]=2[CH:17]=1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 903324625-bromo-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-2-carboxylic acid

생성물 1

HCID 903324825-bromo-N2-methoxy-N2,N3-dimethyl-6-(N-methylmethylsulfonamido)benzofuran-2,3-dicarboxamide수율 62%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 5-bromo-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-2-carboxylic acid (1 g, 2.47 mmol), HOBT (500 mg, 3.70 mmol) and EDCI (946 mg, 4.94 mmol) in DMF (20 mL) was stirred at room temperature under N2 for 2 h. Et3N (1.25 g, 12.34 mmol) and N,O-dimethylhydroxylamine hydrochloride (1.03 g, 12.34 mmol) were added, then the mixture was stirred for 18 h. The mixture was concentrated, diluted with water, extracted with EA, the organic layers were washed with Na2CO3 (a.q.), brine, dried over Na2SO4, concentrated. The residue was purified by column chromatography (DCM:EA=20:1) to get product 5-bromo-N2-methoxy-N2,N3-dimethyl-6-(N-methylmethylsulfonamido)benzofuran-2,3-dicarboxamide (0.68 g, yield: 62%). 1H-NMR (CDCl3, 400 MHz) δ 8.83 (s, 1H), 8.74 (s, 1H), 7.72 (s, 1H), 3.89 (s, 3H), 3.42 (s, 3H), 3.34 (s, 3H), 3.08 (s, 3H), 2.98 (d, J=4.8 Hz, 3H). MS (M+H)+: 448/450.

후처리

  1. stirringthe mixture was stirred for 18 h
  2. concentrationThe mixture was concentrated
  3. additiondiluted with water
  4. extractionextracted with EA
  5. washthe organic layers were washed with Na2CO3 (a.q.), brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (DCM:EA=20:1)

출처 및 근거

ORD 기록
ord-6cea061b9ef04f809c36faf8883736b2
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09243002B2

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