Ammonium Hydroxide → HCID 58237121, compound

HRID 1188939Notes

Reaction equation

HRID 1188939 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][N:19]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14](O)=[O:15])=[CH:10]2)[CH3:3].O[N:29]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[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][N:19]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]([NH2:29])=[O:15])=[CH:10]2)[CH3:3]

Participants

7

Reactant 4

HCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58237057HCID 58237057, compound

Product 1

HCID 58237121HCID 58237121, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 7-(1-methylethoxy)-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indole-2-carboxylic acid (4.0 g), 1-hydroxybenzotriazole (2.07 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.93 g) and N,N-dimethylformamide (50 mL) was stirred at 50° C. for 30 min, and then cooled to room temperature. An aqueous solution of ammonium hydroxide (10%, 10 mL) was added to the mixture. The whole was stirred at room temperature for 12 h. Water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water, saturated aqueous solution of sodium hydrogen carbonate, and brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was crystallized from diisopropyl ether-ethyl acetate to give the title compound (2.26 g, 57%) as brown crystals. MS 390 (MH+).

Workup

  1. temperaturecooled to room temperature
  2. stirringThe whole was stirred at room temperature for 12 h
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with water, saturated aqueous solution of sodium hydrogen carbonate, and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystallized from diisopropyl ether-ethyl acetate

Sources & evidence

ORD record
ord-a381cfd9c44c4e5a8062e85d8cf66130
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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