Hydrochloric Acid → HCID 17859325, compound

HRID 1372701Notes

Reaction equation

HRID 1372701 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH3:20])[CH:12]=2)=[O:10])=[CH:6][CH:5]=[C:4]([CH2:21][C:22]([O:24]CC)=[O:23])[N:3]=1.[OH-].[Na+].CO.O.Cl>C1COCC1>[Cl:1][C:2]1[C:7]([NH:8][C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH3:20])[CH:12]=2)=[O:10])=[CH:6][CH:5]=[C:4]([CH2:21][C:22]([OH:24])=[O:23])[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22242641Methanol--water (1/1)HCID 58779076HCID 58779076, compound

Product 1

HCID 17859325HCID 17859325, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-chloro-3-(1-methyl-3-indolylcarbonyl)amino-6-pyridylacetate (859 mg, 2.31 mmol) was dissolved in THF (25 ml). To the resulting solution was added 0.25N NaOH (13.9 ml, 3.47 mmol), followed by stirring at room temperature for 4 hours. Methanol-water (1:1, v/v, 10 ml) was added, and the mixture was stirred at 50° C. for 2 hours. The reaction mixture was acidified with 1N HCl (5.0 ml). The crystals thus precipitated were collected by filtration, washed with water, and dried under reduced pressure to give 2-chloro-3-(1-methyl-3-indolylcarbonyl)amino-6-pyridylacetyl acid (702 mg, 88%) as a colorless solid.

Workup

  1. stirringthe mixture was stirred at 50° C. for 2 hours
  2. customThe crystals thus precipitated
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. customdried under reduced pressure
  6. customto give 2-chloro-3-(1-methyl-3-indolylcarbonyl)amino-6-pyridylacetyl acid (702 mg, 88%) as a colorless solid

Sources & evidence

ORD record
ord-67fff8100ada427484532e9f8f26d681
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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