Trifluoroacetic acid → HCID 178498369, 화합물

HRID 44522

반응식

HRID 44522 반응식
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][C:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:19](O)([C:21]([F:24])([F:23])[F:22])=O>>[N:13]1([C:9]2[CH:8]=[C:3]([C:4]([O:6][CH3:7])=[O:5])[C:2]3[NH:1][C:19]([C:21]([F:24])([F:23])[F:22])=[N:12][C:11]=3[CH:10]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

참가 물질

3

반응물 2

HCID 6422Trifluoroacetic acidHCID 58279190Methyl 2,3-diamino-5-morpholinobenzoate

생성물 1

HCID 178498369HCID 178498369, 화합물

실험 절차

A mixture of methyl 2,3-diamino-5-(4-morpholinyl)benzoate (4.0 g) in CF3COOH (20 mL) was heated at reflux temperature for 8 h. When TLC analysis indicated consumption of starting material, the mixture was cooled to room temperature and the solvent was removed in-vacuo. The residue was diluted with aqueous NaHCO3 and extracted with EtOAc (250 mL×3). The combined organic layers were washed with brine (250 mL×2), dried over anhydrous Na2SO4. After filtration, the solvent was removed by rotary evaporator. The residue was then purified by silica gel chromatography eluted with EtOAc:petroleum ether=1:4 to afford the desired product as a pale solid. (4.3 g, 82.7%). 1H NMR (300 MHz, DMSO-d6): δ ppm 13.47 (s, 1H), 7.71 (s, 1H), 7.56 (s, 1H), 3.96 (s, 3H), 3.79 (t, 4H, J=4.5 Hz), 3.17 (s, 4H). LC-MS: m/e=330.1 [M+1]+.

후처리

  1. temperaturewas heated
  2. temperatureat reflux temperature for 8 h
  3. customconsumption of starting material
  4. customthe solvent was removed in-vacuo
  5. additionThe residue was diluted with aqueous NaHCO3
  6. extractionextracted with EtOAc (250 mL×3)
  7. washThe combined organic layers were washed with brine (250 mL×2)
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationAfter filtration
  10. customthe solvent was removed by rotary evaporator
  11. customThe residue was then purified by silica gel chromatography
  12. washeluted with EtOAc

출처 및 근거

ORD 기록
ord-c497d058a0b34b9f8363e1ebb4347e19
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541411B2

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