Hydrochloric Acid → 2-(4-{[(4-Bromo-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-6-chloroisonicotinic acid

HRID 2233939Notes

Reaction equation

HRID 2233939 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:18]=[C:19]([CH:24]=[C:25]([Cl:27])[N:26]=3)[C:20]([O:22]C)=[O:21])[CH2:13][CH2:12]2)=[O:9])[NH:5][C:6]=1[CH3:7].[OH-].[Li+].Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:18]=[C:19]([CH:24]=[C:25]([Cl:27])[N:26]=3)[C:20]([OH:22])=[O:21])[CH2:13][CH2:12]2)=[O:9])[NH:5][C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86608287Methyl 2-(4-{[(4-bromo-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-6-chloroisonicotinate

Product 1

HCID 866082882-(4-{[(4-Bromo-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-6-chloroisonicotinic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(4-{[(4-bromo-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-6-chloroisonicotinate (Example 43, 1.7 g, 3.72 mmol) was dissolved in THF (10 ml). 2 N lithium hydroxide (10 ml) was added and the reaction was stirred at room temperature for 3 h. The mixture was acidified with 1 N HCl and was extracted with EtOAc (3×50 ml), dried over Na2SO4 and concentrated in vacuo.

Workup

  1. extractionwas extracted with EtOAc (3×50 ml)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-00a687370d7d476cba6d6dc23273c800
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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