Water → HCID 86728491, compound

HRID 2277780Notes

Reaction equation

HRID 2277780 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16]C(=O)C)[C:11]=1[F:20])[C:6](=O)[CH3:7])[CH3:2].[C:22]1(C=C[CH:27]=[C:25](O)[CH:24]=1)[OH:23].[CH3:30][S:31]([OH:34])(=[O:33])=[O:32].O>C(OCC)(=O)C.C(O)C>[CH3:30][S:31]([OH:34])(=[O:33])=[O:32].[F:20][C:11]1[C:12]([NH2:16])=[N:13][CH:14]=[CH:15][C:10]=1[CH2:9][C:5]1[C:4](=[O:21])[O:3][C:1]2[CH:2]=[C:22]([OH:23])[CH:24]=[CH:25][C:27]=2[C:6]=1[CH3:7]

Participants

7

Reactant 4

HCID 962Water2×HCID 5054ResorcinolHCID 6395Methanesulfonic AcidHCID 86728492HCID 86728492, compound

Product 1

HCID 86728491HCID 86728491, compoundYield 60.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere, the oily product of step 3 (2.70 g) was dissolved in ethyl acetate (5.47 mL), resorcinol (1.32 g, 12.0 mmol) and methanesulfonic acid (8.20 mL, 126 mmol) were added while stirring at room temperature, and after warming to 50° C., the mixture was stirred for 4 hours. The reaction mixture was cooled to room temperature and allowed to stand for 16 hours, water (2.7 mL) was then added, and the mixture was stirred at 80° C. for 7 hours. The reaction mixture was again cooled to room temperature and allowed to stand for 16 hours, and after the mixture was warmed to 70° C., seed crystals (27.4 mg) were added. Water (5.5 mL) was then added, the mixture was stirred for 1 hour, ethanol (13.7 mL) was further added, and the mixture was stirred for 30 minutes. It was then cooled to 25° C., ethanol (38.2 mL) was added, and the mixture was stirred for 30 minutes. The precipitated crystals were collected by filtration, washed twice with ethanol (16.4 mL), and dried under reduced pressure to obtain the title compound (2.20 g).

Workup

  1. temperatureafter warming to 50° C.
  2. stirringthe mixture was stirred for 4 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. stirringthe mixture was stirred at 80° C. for 7 hours
  5. temperatureThe reaction mixture was again cooled to room temperature
  6. waitto stand for 16 hours
  7. temperatureafter the mixture was warmed to 70° C.
  8. stirringthe mixture was stirred for 1 hour
  9. stirringthe mixture was stirred for 30 minutes
  10. temperatureIt was then cooled to 25° C.
  11. stirringthe mixture was stirred for 30 minutes
  12. filtrationThe precipitated crystals were collected by filtration
  13. washwashed twice with ethanol (16.4 mL)
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-36a69e1367b54b2bbae0b6e17d3fc036
Source dataset
uspto-grants-2015_09
Patent number
US09133174B2

Reaction notes

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