Trifluoroacetic acid → HCID 178498369, compound

HRID 1749614Notes

Reaction equation

HRID 1749614 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

HCID 178498369HCID 178498369, compound

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-ad55713d1ca64dbe9761aaee3e607e61
Source dataset
uspto-grants-2015_10
Patent number
US09156797B2

Reaction notes

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