Ammonium Hydroxide → HCID 66897826, compound

HRID 1188942Notes

Reaction equation

HRID 1188942 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[C:18]([O:20][CH:21]([CH3:23])[CH3:22])[CH:19]=2)[NH:16][C:15]([C:24](O)=[O:25])=[CH:14]3)=[CH:6][CH:5]=1.O[N:28]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[OH-].[NH4+]>O.CN(C)C=O>[CH3:1][O:2][CH2:3][C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[C:18]([O:20][CH:21]([CH3:22])[CH3:23])[CH:19]=2)[NH:16][C:15]([C:24]([NH2:28])=[O:25])=[CH:14]3)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66897952HCID 66897952, compound

Product 1

HCID 66897826HCID 66897826, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-{[6-(methoxymethyl)pyridin-3-yl]oxy}-7-(1-methylethoxy)-1H-indole-2-carboxylic acid (1.43 g), 1-hydroxybenzotriazole (810 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.15 g) and N,N-dimethylformamide (50 mL) was stirred at room temperature for 30 min. An aqueous solution of ammonium hydroxide (25%, 5 mL) was added to the mixture. The whole was stirred at room temperature for 4.5 days. 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 washed with diisopropyl ether to give the title compound (1.05 g, 74%) as pale brown crystals. MS 356 (MH+).

Workup

  1. stirringThe whole was stirred at room temperature for 4.5 days
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed successively with water, saturated aqueous solution of sodium hydrogen carbonate and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-d1324dca2cc34abd8a1f888cd53fec30
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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