Hydrochloric Acid → HCID 136202039, compound

HRID 2075973Notes

Reaction equation

HRID 2075973 reaction equation
[OH:1][C:2]1[C:3]([N+:19]([O-:21])=[O:20])=[C:4]([C:9]([C:13]2[N:17]=[C:16]([CH3:18])[O:15][N:14]=2)=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[CH2:22]([N:24]([CH2:28][CH3:29])[C:25](Cl)=[O:26])[CH3:23].N1C=CC=CC=1.Cl>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH2:22]([N:24]([CH2:28][CH3:29])[C:25]([O:12][C:11]1[CH:10]=[C:9]([C:13]2[N:17]=[C:16]([CH3:18])[O:15][N:14]=2)[C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([N+:19]([O-:21])=[O:20])[C:2]=1[OH:1])=[O:26])[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6916Diethylcarbamoyl chlorideHCID 135911996HCID 135911996, compound2×

Product 1

HCID 136202039HCID 136202039, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 3,4-dihydroxy-6-(5-methyl-[1,2,4]-oxadiazol-3-yl)-2-nitrobenzoate (compound 1-5) (50 mg), diethylcarbamoyl chloride (0.024 mL), 4-dimethylaminopyridine (4 mg) and pyridine (2 mL) was stirred at room temperature for 3 hours. After addition of ethyl acetate, the mixture was acidified with 2 mol/L hydrochloric acid. The separated organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 20%-100% ethyl acetate/hexane, gradient elution) to give the title compound (31 mg). The structural formula was illustrated in table 13.

Workup

  1. washThe separated organic layer was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: 20%-100% ethyl acetate/hexane, gradient elution)

Sources & evidence

ORD record
ord-82776452449b4371bdd77d7fe018f7ac
Source dataset
uspto-grants-2011_04
Patent number
US07923462B2

Reaction notes

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