Ammonium Hydroxide → 7-Methoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxamide

HRID 1188910Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:15][C:16]2[CH:17]=[N:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([OH:14])=O)=[CH:8]2.Cl.C([N:29]=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]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([NH2:29])=[O:14])=[CH:8]2

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 7-methoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indole-2-carboxylic acid (0.9 g), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.95 g), 1-hydroxybenzotriazole (0.67 g) and N,N-dimethylformamide (15 mL) was stirred at 50° C. for 20 min. The mixture was cooled to room temperature, and 10% aqueous ammonium hydroxide solution (2 mL) was added to the mixture. After stirring at room temperature for 2 h, the mixture was concentrated under reduced pressure. Water was added to the residue and the resulting yellow suspension was filtered to give the title compound (0.66 g, 74%) as a yellow solid. MS 362 (MH+).

Workup

temperatureThe mixture was cooled to room temperature
stirringAfter stirring at room temperature for 2 h
concentrationthe mixture was concentrated under reduced pressure
additionWater was added to the residue
filtrationthe resulting yellow suspension was filtered

Sources & evidence

ORD record: ord-3878696d677449978627d939f789ada6
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673942B2

Reaction notes

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