Sulfuric Acid → HCID 69888011, compound

HRID 352085Notes

Reaction equation

HRID 352085 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.[S:35](=[O:39])(=[O:38])([OH:37])[OH:36]>C(OCC)(=O)C.O1CCCC1>[S:35]([OH:39])([OH:38])(=[O:37])=[O:36].[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 1118Sulfuric AcidHCID 6444692Mubritinib

Product 1

HCID 69888011HCID 69888011, compoundYield 93.6%

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 sulfuric acid (209 mg) in tetrahydrofuran (5 ml) was added dropwise. The crystals were precipitated. The mixture was stirred at room temperature for 40 min and filtrated. The mixture was washed with ethyl acetate (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 sulfate (1.13 g, yield 93%).

Workup

  1. customThe crystals were precipitated
  2. filtrationfiltrated
  3. washThe mixture was washed with ethyl acetate (3 ml)
  4. customdried under reduced pressure (40° C.)

Sources & evidence

ORD record
ord-dcb80f521c514c9e9f444353cc748963
Source dataset
uspto-grants-2004_06
Patent number
US06743924B2

Reaction notes

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