1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 58237016, compound

HRID 1188937Notes

Reaction equation

HRID 1188937 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([CH3:29])[O:5][C:6]1[CH:7]=[C:8]([O:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15](O)=[O:16])=[CH:11]2.Cl.C([N:33]=C=NCCCN(C)C)C.[NH4+].ON1C2C=CC=CC=2N=N1>CN(C)C=O>[CH3:1][O:2][CH2:3][CH:4]([CH3:29])[O:5][C:6]1[CH:7]=[C:8]([O:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([NH2:33])=[O:16])=[CH:11]2

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 58237058HCID 58237058, compound

Product 1

HCID 58237016HCID 58237016, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(2-methoxy-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylic acid (1.072 g) in N,N-dimethylformamide (15 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.98 g) and 1-hydroxybenzotriazole ammonium salt (0.788 g) at room temperature. The mixture was stirred at room temperature for 1 h. The mixture was concentrated in vacuo. Water and ethyl acetate were added to the residue and the resultant was extracted with ethyl acetate. The organic layer was washed successively with brine and water, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate: methanol=100:0 to 95:5, volume ratio) to give the title compound. (910 mg, 85%) as a white amorphous solid. MS 419 (MH+).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionWater and ethyl acetate were added to the residue
  3. extractionthe resultant was extracted with ethyl acetate
  4. washThe organic layer was washed successively with brine and water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (ethyl acetate: methanol=100:0 to 95:5, volume ratio)

Sources & evidence

ORD record
ord-9c1793258e5d490aa2f822fac5e1758e
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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