Trifluoroacetic acid → (3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4H-chromeno[3,4-d]isoxazol-7-yl)methanol

HRID 1506430Notes

Reaction equation

HRID 1506430 reaction equation
O1CCN([C:7]23[C:34]4[CH:33]=[CH:32][C:31]([CH2:35][OH:36])=[CH:30][C:29]=4[O:28][CH2:27][CH:8]2[C:9]([C:12]2[O:16][N:15]=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:13]=2[C:23]([F:26])([F:25])[F:24])=[N:10][O:11]3)CC1.C(O)(C(F)(F)F)=O>ClC(Cl)C.ClCCl>[C:17]1([C:14]2[C:13]([C:23]([F:26])([F:25])[F:24])=[C:12]([C:9]3[C:8]4[CH2:27][O:28][C:29]5[CH:30]=[C:31]([CH2:35][OH:36])[CH:32]=[CH:33][C:34]=5[C:7]=4[O:11][N:10]=3)[O:16][N:15]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67169503(9b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazol-7-yl)methanol

Product 1

HCID 67169318(3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4H-chromeno[3,4-d]isoxazol-7-yl)methanolYield 47%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (9b-morpholino-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,9b-dihydro-3aH-chromeno[3,4-d]isoxazol-7-yl)methanol (Preparation 60G 0.070 g, 0.140 mmol) in dichloroethane (1.0 mL) at room temperature was added TFA (0.016 mL, 0.209 mmol). The reaction mixture was heated at 80° C. for 60 min. The reaction mixture was diluted with dichloromethane, washed with a saturated aqueous solution of sodium bicarbonate, and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded a pale yellow solid which was triturated with methanol with sonication and dried to give (3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4H-chromeno[3,4-d]isoxazol-7-yl)methanol (0.027 g, 0.065 mmol, 47% yield) as a white solid. The product had an HPLC ret. time=3.18 min.−Column: Chromolith SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA. LC/MS M+1=414.9.

Workup

  1. washwashed with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationConcentration under reduced pressure
  4. customafforded a pale yellow solid which
  5. customwas triturated with methanol with sonication
  6. customdried

Sources & evidence

ORD record
ord-f74f6cedd6fa41248b030f4960d1aca8
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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