Water → HCID 11855227, compound

HRID 1162914Notes

Reaction equation

HRID 1162914 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:16]=[C:15]3[C:10]([CH:11]=[C:12]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:24]([F:27])([F:26])[F:25])[NH:13][C:14]3=[O:17])=[CH:9][CH:8]=2)[CH2:5][CH:4]([C:28]([OH:30])=O)[O:3]1.[NH4+].[OH-].[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)[N:37]=1.O>C(O)(C)C>[O:1]=[C:2]1[N:6]([C:7]2[CH:16]=[C:15]3[C:10]([CH:11]=[C:12]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:24]([F:25])([F:26])[F:27])[NH:13][C:14]3=[O:17])=[CH:9][CH:8]=2)[CH2:5][CH:4]([C:28]([NH2:37])=[O:30])[O:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 11855226HCID 11855226, compound

Product 1

HCID 11855227HCID 11855227, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The 2-oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]oxazolidin-5-carboxylic acid (12.5 mg, 0.03 mmol) obtained in Example 2-4 and a 25% ammonia aqueous solution (3.06 μl, 0.045 mmol) were dissolved in isopropanol (0.3 ml). Thereafter, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (13.3 mg, 0.045 mmol) was added to the solution, and the obtained mixture was then stirred at a room temperature for 3.5 hours. Thereafter, water was added to the reaction solution, and the mixture was then extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was then distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=30:1), so as to obtain 2-oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]oxazolidin-5-carboxylic amide (9.8 mg, 78%) in the form of a colorless amorphous substance.

Workup

  1. extractionthe mixture was then extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. distillationthe solvent was then distilled away under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=30:1)

Sources & evidence

ORD record
ord-8ef3dbe44fbf45b1932c14c54b96a83e
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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