Citric Acid → HCID 57901839, compound

HRID 1851468Notes

Reaction equation

HRID 1851468 reaction equation
CON(C)[C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[NH:15][S:16]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)(=[O:18])=[O:17])=[O:5].C[Li].[C:27](O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.C(OCC)C>[C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[NH:15][S:16]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)(=[O:18])=[O:17])(=[O:5])[CH3:27]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 57901630HCID 57901630, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 57901839HCID 57901839, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-methoxy-N-methyl-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (160 mg) in anhydrous tetrahydrofuran (10 mL) was cooled to −70° C. under nitrogen atmosphere. A solution (1.8 mL) of 1.2M-methyllithium in diethyl ether was added dropwise. The temperature of the solution was gradually raised from −70° C. to 0° C., and the mixture was stirred for 4 hr. The reaction mixture was poured into aqueous citric acid solution, and the mixture was extracted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:10-3:7), and the obtained crystals were washed with ethyl acetate-hexane to give the title compound (22 mg, yield 16%) as colorless crystals. melting point 241-243° C.

Workup

  1. temperatureThe temperature of the solution was gradually raised from −70° C. to 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washthe obtained crystals were washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-059770ae64014050b617b469e95df969
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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