Ammonium Hydroxide → HCID 66897756, compound

HRID 1188929Notes

Reaction equation

HRID 1188929 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([CH2:29][O:30][CH3:31])[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][N:20]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([OH:17])=O)=[CH:11]2.Cl.C([N:35]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[OH-].[NH4+]>CN(C)C=O>[CH3:1][O:2][CH2:3][CH:4]([CH2:29][O:30][CH3:31])[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:26])=[O:27])=[CH:21][N:20]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([NH2:35])=[O:17])=[CH:11]2

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66897332HCID 66897332, compound

Product 1

HCID 66897756HCID 66897756, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 7-[2-methoxy-1-(methoxymethyl)ethoxy]-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indole-2-carboxylic acid (1.66 g), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.4 g), 1-hydroxybenzotriazole (1.0 g) and N,N-dimethylformamide (15 mL) was stirred at 50° C. for 30 min. The mixture was cooled to room temperature, and 25% ammonium hydroxide solution (1.5 mL) was added to the mixture. After stirring at room temperature for 14 h, the mixture was concentrated under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by basic silica gel column chromatography (methanol/ethyl acetate/hexane=0/60/40 to 10/90/0, volume ratio) to give the title compound (1.66 g, 100%) as a colorless amorphous solid. MS 450 (MH+).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. stirringAfter stirring at room temperature for 14 h
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by basic silica gel column chromatography (methanol/ethyl acetate/hexane=0/60/40 to 10/90/0, volume ratio)

Sources & evidence

ORD record
ord-42356dcc1da84cf38052c965e42fa724
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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