Methanesulfonic Acid → 1-[4-[4-[[2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methoxy]phenyl]butyl]-1H-1,2,3-triazole methanesulfonate

HRID 352082

Reaction equation

HRID 352082 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]2[O:12][CH:13]=[C:14]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][N:28]4[CH:32]=[CH:31][N:30]=[N:29]4)=[CH:20][CH:19]=3)[N:15]=2)=[CH:5][CH:4]=1.[CH3:35][S:36]([OH:39])(=[O:38])=[O:37]>C(OCC)(=O)C.O1CCCC1>[CH3:35][S:36]([OH:39])(=[O:38])=[O:37].[F:34][C:2]([F:1])([F:33])[C:3]1[CH:4]=[CH:5][C:6](/[CH:9]=[CH:10]/[C:11]2[O:12][CH:13]=[C:14]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][N:28]4[CH:32]=[CH:31][N:30]=[N:29]4)=[CH:20][CH:19]=3)[N:15]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 6444692Mubritinib

Product 1

HCID 865876351-[4-[4-[[2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methoxy]phenyl]butyl]-1H-1,2,3-triazole methanesulfonateYield 98%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1-[4-[4-[[2-[(E)-2-[4-(Trifluoromethyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methoxy]phenyl]butyl]-1H-1,2,3-triazole (1.0 g) was dissolved in ethyl acetate (50 ml) and tetrahydrofuran (5 ml). A solution of methanesulfonic acid (205 mg) in tetrahydrofuran (5 ml) was added dropwise. The crystals were precipitated. The mixture was stirred at room temperature for 20 min and under ice-cooling for 50 min. The reaction mixture was concentrated under reduced pressure until the liquid amount became about half. After stirring the mixture under ice-cooling for 30 min, the mixture was filtrated, washed with ethyl acetate/isopropyl ether=1/1 (3 ml) and dried under reduced pressure (40° C.) to give 1-[4-[4-[ [2-[ (E)-2-[4-(trifluoromethyl)-phenyl]ethenyl]-1,3-oxazol-4-yl]methoxy]phenyl]butyl]-1H-1,2,3-triazole methanesulfonate (1.18 g, yield 98%).

Workup

  1. customThe crystals were precipitated
  2. temperaturecooling for 50 min
  3. concentrationThe reaction mixture was concentrated under reduced pressure until the liquid amount
  4. stirringAfter stirring the mixture under ice-
  5. temperaturecooling for 30 min
  6. filtrationthe mixture was filtrated
  7. washwashed with ethyl acetate/isopropyl ether=1/1 (3 ml)
  8. customdried under reduced pressure (40° C.)

Sources & evidence

ORD record
ord-b1868528949c4af58571335dcb643808
Source dataset
uspto-grants-2004_06
Patent number
US06743924B2

Linked notes

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