Hydrochloric Acid → N-(4-Acetyl-2-cyano-5-fluoro-6-hydroxy-3-methylphenyl)cyclopropanecarboxamide

HRID 17341

Reaction equation

HRID 17341 reaction equation
[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:20]#[N:21])[C:10]([CH3:19])=[C:11]([C:14]([O:16]CC)=[CH2:15])[C:12]=3[F:13])[N:8]=2)[CH2:3][CH2:2]1.Cl.[O:23]1C=CN=C1.CO>O1CCCC1>[C:14]([C:11]1[C:12]([F:13])=[C:6]([OH:5])[C:7]([NH:8][C:4]([CH:1]2[CH2:2][CH2:3]2)=[O:23])=[C:9]([C:20]#[N:21])[C:10]=1[CH3:19])(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 9255OxazoleHCID 685864422-Cyclopropyl-6-[1-(ethoxy)ethenyl]-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 86630836N-(4-Acetyl-2-cyano-5-fluoro-6-hydroxy-3-methylphenyl)cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Cyclopropyl-6-[1-(ethoxy)ethenyl]-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-78) (1.0 g, 3.49 mmol) was dissolved in tetrahydrofuran (10 ml), aqueous 1 N hydrochloric acid solution (2.0 ml) was added, followed by stirring at room temperature for 19 hours. At this point in time, it was known that a mixture with an oxazole-opened compound is given, and for complete ring opening, methanol (5 ml) was added followed by stirring overnight at room temperature. The solvent was concentrated under reduced pressure, ethyl acetate was added to the resulting residue, followed by fractionation with water.

Workup

  1. stirringby stirring overnight at room temperature
  2. concentrationThe solvent was concentrated under reduced pressure, ethyl acetate
  3. additionwas added to the resulting residue

Sources & evidence

ORD record
ord-aa3e8be5607b4c5db95471ff710fd6d1
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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