Mubritinib → HCID 22715033, compound

HRID 352084Notes

Reaction equation

HRID 352084 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.O.[C:36]1([S:42]([OH:45])(=[O:44])=[O:43])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(OCC)(=O)C.O1CCCC1>[C:36]1([S:42]([OH:45])(=[O:44])=[O:43])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[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 6444692MubritinibHCID 15619088Hydroxybenzenesulfonic acid

Product 1

HCID 22715033HCID 22715033, compoundYield 78.5%

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 benzenesulfonic acid monohydrate (376 mg) in tetrahydrofuran (5 ml) was added dropwise. The crystals were precipitated. The mixture was stirred room temperature for 2 hours and filtrated. The mixture was 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 benzenesulfonate (1.05 g, yield 78%).

Workup

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

Sources & evidence

ORD record
ord-fe433aeb75464c87a7189e0d7cc37abe
Source dataset
uspto-grants-2004_06
Patent number
US06743924B2

Reaction notes

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