Ammonium Hydroxide → HCID 66897666, compound

HRID 1188894Notes

Reaction equation

HRID 1188894 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]([OH:16])=O)=[CH:10]2)[CH3:3].Cl.C([N:31]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[OH-].[NH4+]>O.CN(C)C=O>[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]([NH2:31])=[O:16])=[CH:10]2)[CH3:3]

Participants

7

Reactant 4

HCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66897529HCID 66897529, compound

Product 1

HCID 66897666HCID 66897666, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 7-(1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylic acid (1.8 g), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.77 g), 1-hydroxybenzotriazole (1.24 g) and N,N-dimethylformamide (45 mL) was stirred at 50° C. for 25 min. The mixture was cooled to room temperature, and 28% aqueous ammonium hydroxide solution (1.3 mL) was added to the mixture at room temperature. After stirring at room temperature for 16 h, water was added to the mixture. 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 silica gel column chromatography (ethyl acetate/hexane=20/80 to 100/0, volume ratio) to give the title compound (1.41 g, 79%) as a white solid. MS 389 (MH+).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. stirringAfter stirring at room temperature for 16 h
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80 to 100/0, volume ratio)

Sources & evidence

ORD record
ord-df41b750a2e244e393db770f9de3497c
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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