Hydrochloric Acid → HCID 59478050, compound

HRID 570824Notes

Reaction equation

HRID 570824 reaction equation
[C:1]([C:3]1[C:4]([C:8]([OH:10])=O)=[CH:5][NH:6][CH:7]=1)#[N:2].Cl.CN.O[N:15]1[C:19]2C=CC=CC=2N=N1.Cl>O1CCCC1.C(N(CC)CC)C>[CH3:19][NH:15][C:8]([C:4]1[C:3]([C:1]#[N:2])=[CH:7][NH:6][CH:5]=1)=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 6364545Methylamine hydrochlorideHCID 59477562HCID 59477562, compound

Product 1

HCID 59478050HCID 59478050, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-cyano-1H-pyrrole-3-carboxylic acid (0.034 g), methylamine hydrochloride (0.034 g), triethylamine (0.084 g) and 1-hydroxybenzotriazole (0.034 g) in tetrahydrofuran (2.5 mL) was added N-ethyl-N′-3-dimethylaminopropylcarbodiimide (0.058 g) at room temperature, and this mixture was stirred at same 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, and 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) to give the title compound (0.035 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)

Sources & evidence

ORD record
ord-d082445672bb4325ac20b81120919606
Source dataset
uspto-grants-2015_05
Patent number
US09023882B2

Reaction notes

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