Hydrochloric Acid → 6-Chloro-4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)quinoline-2-carboxylic acid

HRID 2234036Notes

Reaction equation

HRID 2234036 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([O:14]C)=[O:13])[CH:6]=[C:5]2[N:16]1[CH2:21][CH2:20][CH:19]([NH:22][C:23]([C:25]2[NH:26][C:27]([CH3:32])=[C:28]([Cl:31])[C:29]=2[Cl:30])=[O:24])[CH2:18][CH2:17]1.[OH-].[Na+].Cl>C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[C:5]2[N:16]1[CH2:17][CH2:18][CH:19]([NH:22][C:23]([C:25]2[NH:26][C:27]([CH3:32])=[C:28]([Cl:31])[C:29]=2[Cl:30])=[O:24])[CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68582528HCID 68582528, compound

Product 1

HCID 113750776-Chloro-4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)quinoline-2-carboxylic acidYield 94.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl 6-chloro-4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)quinoline-2-carboxylate (Example 134; 20 mg) was dissolved in 6 ml of 2:1 THF/MeOH, 0.20 ml of 1 N NaOH was added and the resulting solution was stirred at ambient temperature for 20 h. Following neutralization with 0.25 ml of 1 N HCl, the reaction was diluted with 5 ml of water and filtered. The solid was washed with water and dried under vacuum, giving 18.4 mg of a light yellow granular solid.

Workup

  1. filtrationfiltered
  2. washThe solid was washed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-9112525113944fba94c1a1bfa35399fd
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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