Hydrochloric Acid → HCID 59606505, compound

HRID 502244Notes

Reaction equation

HRID 502244 reaction equation
C[O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:29]#[N:30])=[C:10]([C:16]3[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])=[CH:18][CH:17]=3)[N:11]2[CH2:14][CH3:15])=[CH:7][CH:6]=1)=[O:4].NC1C=CC(C2N(CC)C3C(C=2C#N)=CC=C(C(OC)=O)C=3)=CC=1.[OH-].[K+].Cl>>[C:29]([C:9]1[C:8]2[C:12](=[CH:13][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=2)[N:11]([CH2:14][CH3:15])[C:10]=1[C:16]1[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH2:26][CH2:27][CH3:28])(=[O:24])=[O:25])=[CH:18][CH:17]=1)#[N:30]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59426442HCID 59426442, compoundHCID 59606417HCID 59606417, compound

Product 1

HCID 59606505HCID 59606505, compoundYield 96%

Procedure

3-Cyano-1-ethyl-2-[4-(propane-1-sulfonylamino)-phenyl]-1H-indole-6-carboxylic acid methyl ester (1.25 g, 3.04 mmol), prepared by the method described in example 1Y from methyl 2-(4-aminophenyl)-3-cyano-1-ethyl-1H-indole-6-carboxylate, is treated with 0.5N KOH (30 mL, 15.2 mmol) and heated at reflux for 2.5 h. After cooling to room temperature, the aqueous phase is acidified with 3N HCl to pH 2 and the resultant precipitate is filtered, washed with water (2×) and dried until constant weight to afford 1.15 g (96%) of 3-cyano-1-ethyl-2-[4-(propane-1-sulfonylamino)-phenyl]-1H-indole-6-carboxylic acid as a white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2.5 h
  3. filtrationthe resultant precipitate is filtered
  4. washwashed with water (2×)
  5. customdried until constant weight

Sources & evidence

ORD record
ord-a4beef94efc44c9bb03c5bb6b2bf244c
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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