N,N-Dimethylethylenediamine → HCID 24743339, compound

HRID 1514653Notes

Reaction equation

HRID 1514653 reaction equation
[C:1]([C:5]1[N:9]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:8]([CH3:19])=[C:7]([C:20](O)=[O:21])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH3:45][N:46]([CH3:50])[CH2:47][CH2:48][NH2:49]>CN(C)C=O>[C:1]([C:5]1[N:9]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:8]([CH3:19])=[C:7]([C:20]([NH:49][CH2:48][CH2:47][N:46]([CH3:50])[CH3:45])=[O:21])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66670176HCID 66670176, compound

Product 1

HCID 24743339HCID 24743339, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 910 mg portion of 5-tert-butyl-1-[2-(4-fluorophenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxylic acid was dissolved in 10 ml of N,N-dimethylformamide, and under ice-cooling 748 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 527 mg of 1-hydroxybenzotriazole were added, followed by stirring at the same temperature for 1 hour. A 0.65 ml portion of N,N-dimethylethane-1,2-diamine was added to the reaction liquid, and after stirring at room temperature for 15 hours, the solvent was evaporated under a reduced pressure. Ethyl acetate was added to the residue and, after washing with a saturated sodium bicarbonate aqueous solution, water and saturated brine, the organic layer was dried over anhydrous magnesium sulfate. After evaporation of the solvent under a reduced pressure, the residue was washed with ethyl acetate to obtain 783 mg of 5-tert-butyl-N-[2-(dimethylamino)ethyl]-1-[2-(4-fluorophenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxamide as a colorless solid. A 783 mg portion of this product was dissolved in 5 ml of methanol, and 1 ml of 4 M hydrogen chloride/ethyl acetate was added under ice-cooling, followed by stirring at the same temperature for 30 minutes. The solvent was evaporated under a reduced pressure, and the resulting residue was solidified with methanol-ethyl acetate to obtain 360 mg of 5-tert-butyl-N-[2-(dimethylamino)ethyl]-1-[2-(4-fluorophenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxamide as a colorless solid.

Workup

  1. additionwere added
  2. stirringafter stirring at room temperature for 15 hours
  3. customthe solvent was evaporated under a reduced pressure
  4. additionEthyl acetate was added to the residue
  5. washafter washing with a saturated sodium bicarbonate aqueous solution, water and saturated brine
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. customAfter evaporation of the solvent under a reduced pressure
  8. washthe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-1b07d8724433478dafb0b3b2fa2517ec
Source dataset
uspto-grants-2012_07
Patent number
US08222274B2

Reaction notes

Loading…