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Dimethylformamide → N-(2-Methoxyethyl)-6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridinecarboxamide

HRID 499338
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HRID 499338 반응식
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[N:17]=[C:16]([C:18]([OH:20])=O)[CH:15]=[CH:14][CH:13]=2)=[N:3]1.[CH3:21][CH2:22][N:23]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN([CH:45]=[O:46])C>O>[CH3:45][O:46][CH2:21][CH2:22][NH:23][C:18]([C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([C:4]2[S:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:2](=[O:1])[N:3]=2)[N:17]=1)=[O:20]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 229393396-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridinecarboxylic acid

생성물 1

HCID 59750369N-(2-Methoxyethyl)-6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridinecarboxamide수율 40%

시약·촉매·용매 1

HCID 962
Water
용매

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온도
80 °C

실험 절차

A mixture of 6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridinecarboxylic acid (350 mg, 1.2 mmol), WSC (471 mg, 2.4 mmol), HOBt (332 mg, 2.4 mmol) and DMF (10 ml) was stirred at 80° C. for 17 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and dried. The solvent was evaporated. The residue was subjected to a silica gel column chromatography, eluted with ethyl acetate-methanol (50:1, v/v) and recrystallized from tetrahydrofuran-hexane to give the titled compound (167 mg, 40%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customThe solvent was evaporated
  5. washeluted with ethyl acetate-methanol (50:1
  6. customv/v) and recrystallized from tetrahydrofuran-hexane

출처 및 근거

ORD 기록
ord-fd9ff093ff8a45008579c5ac7bb0623b
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07767665B2

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