HCID 90121138, compound → HCID 90109782, compound

HRID 521721Notes

Reaction equation

HRID 521721 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:15][CH:14]3[C:10]([C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)([N:11](CC4C=CC(OC)=CC=4)[O:12][CH2:13]3)[CH2:9]2)=[N:6][CH:7]=1>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:7]=[N:6][C:5]([N:8]2[CH2:15][CH:14]3[C:10]([C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)([NH:11][O:12][CH2:13]3)[CH2:9]2)=[N:4][CH:3]=1

Participants

3

Reactant 1

HCID 90121138HCID 90121138, compound

Product 1

HCID 90109782HCID 90109782, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5-(5-fluoropyrimidin-2-yl)-1-[(4-methoxyphenyl)methyl]-6a-(3-pyridyl)-3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole (1.11 g, 2.32 mmol) in trifluoroacetic acid (9.3 mL) is stirred at 60° C. for 1 hour. The solvent is evaporated and the resulting residue is partitioned between dichloromethane (100 mL) and saturated aqueous sodium carbonate solution (25 mL). The organic phase is separated and the aqueous phase is re-extracted twice with dichloromethane (100 mL). The combined organic extracts are dried over magnesium sulfate, filtered, and the solvent evaporated under vacuum to give a residue that is purified by silica gel chromatography using a 0-10% gradient of 0.14 M ammonia/methanol solution in dichloromethane to give the title compound (0.64 g, 96%). ES/MS (m/e): 288 (M+1).

Workup

  1. customThe solvent is evaporated
  2. customthe resulting residue is partitioned between dichloromethane (100 mL) and saturated aqueous sodium carbonate solution (25 mL)
  3. customThe organic phase is separated
  4. extractionthe aqueous phase is re-extracted twice with dichloromethane (100 mL)
  5. dry with materialThe combined organic extracts are dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated under vacuum
  8. customto give a residue that
  9. customis purified by silica gel chromatography

Sources & evidence

ORD record
ord-c6f8a47845ed4fdd90da3e0c55639783
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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