Ammonium Hydroxide → HCID 66897791, compound

HRID 1188933Notes

Reaction equation

HRID 1188933 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:15][C:16]2[CH:17]=[N:18][C:19]([CH2:22][O:23][CH3:24])=[CH:20][CH:21]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12](O)=[O:13])=[CH:8]2.Cl.C([N:28]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[OH-].[NH4+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:15][C:16]2[CH:17]=[N:18][C:19]([CH2:22][O:23][CH3:24])=[CH:20][CH:21]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([NH2:28])=[O:13])=[CH:8]2

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66897999HCID 66897999, compound

Product 1

HCID 66897791HCID 66897791, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-methoxy-5-{[6-(methoxymethyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylic acid (2.28 g), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.66 g), 1-hydroxybenzotriazole (2.13 g) and N,N-dimethylformamide (30 mL) was stirred at room temperature for 20 min. A solution of 25% ammonium hydroxide (3 mL) was added to the mixture. After stirring at room temperature for 15.5 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 residual oil was solidified with ethyl acetate-diethyl ether and the resulting solid was washed with diethyl ether to give the title compound (1.65 g, 73%) as a pale orange solid. MS 328 (MH+).

Workup

  1. stirringAfter stirring at room temperature for 15.5 h
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washthe resulting solid was washed with diethyl ether

Sources & evidence

ORD record
ord-f520b688dcf643cc856029821e351ea9
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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