Hydrochloric Acid → HCID 58437289, compound

HRID 73370Notes

Reaction equation

HRID 73370 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20](O)=[O:21])=[CH:17][CH:18]=3)[C:13]([C:23]#[N:24])=[CH:12]2)=[CH:7][CH:6]=1)[CH3:2].Cl.[CH3:27][NH:28][CH3:29].C(N(CC)CC)C.Cl>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]([N:28]([CH3:29])[CH3:27])=[O:21])=[CH:17][CH:18]=3)[C:13]([C:23]#[N:24])=[CH:12]2)=[CH:7][CH:6]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 58437256HCID 58437256, compound

Product 1

HCID 58437289HCID 58437289, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5-carboxy-3-cyanoindol-1-yl)benzoic acid ethyl ester (0.084 g), dimethylamine hydrochloride (0.061 g), triethylamine (0.13 g) and 4-dimethylaminopyridine (0.006 g) in dichloromethane (2.5 mL) was added N-ethyl-N′-3-dimethylaminopropylcarbodiimide (0.058 g) at room temperature, and this mixture was stirred at room temperature overnight. This reaction mixture was poured into 1 mol/L hydrochloric acid, and this mixture was extracted with ethyl acetate. This organic layer was washed with a saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/2) to give the title compound (0.020 g).

Workup

  1. extractionthis mixture was extracted with ethyl acetate
  2. washThis organic layer was washed with a saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/2)

Sources & evidence

ORD record
ord-398a862e0f054cdc9d95d87dacc6485b
Source dataset
uspto-grants-2014_09
Patent number
US08829040B2

Reaction notes

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