Hydrochloric Acid → 4-({2-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoyl}amino)benzoic acid

HRID 56997Notes

Reaction equation

HRID 56997 reaction equation
O.[OH-].[Na+].[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([C:37]#[N:38])=[C:9]([C:11]2[C:16]([O:17][CH3:18])=[CH:15][N:14]([CH:19]([CH2:34][CH3:35])[C:20]([NH:22][C:23]3[CH:33]=[CH:32][C:26]([C:27]([O:29]CC)=[O:28])=[CH:25][CH:24]=3)=[O:21])[C:13](=[O:36])[CH:12]=2)[CH:10]=1.Cl>C(O)C>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([C:37]#[N:38])=[C:9]([C:11]2[C:16]([O:17][CH3:18])=[CH:15][N:14]([CH:19]([CH2:34][CH3:35])[C:20]([NH:22][C:23]3[CH:33]=[CH:32][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=3)=[O:21])[C:13](=[O:36])[CH:12]=2)[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 117622810Ethyl 4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoyl}amino)benzoate

Product 1

HCID 1176227544-({2-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoyl}amino)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

At RT, 0.2 ml of water and 97 mg (1.22 mmol, 3.0 eq.) of sodium hydroxide were added to a suspension of 200 mg (0.41 mmol) of ethyl 4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoyl}amino)benzoate (racemate) in 2.0 ml of ethanol. The reaction mixture was stirred at RT for 1 h and at an oil bath temperature of 60° C. for 6 h, allowed to stand at RT overnight and then added to aqueous hydrochloric acid (1N). After dilution with water a precipitate was formed which was filtered off, washed twice with water and dried under reduced pressure. The precipitate was then purified by flash chromatography (25 g of silica gel, mobile phase: dichloromethane→dichloromethane/methanol 50:1). Yield: 144 mg (38% of theory based on 0.82 mmol, since two crude product batches of the stated size were purified together)

Workup

  1. waitto stand at RT overnight
  2. filtrationwas filtered off
  3. washwashed twice with water
  4. customdried under reduced pressure
  5. customThe precipitate was then purified by flash chromatography (25 g of silica gel, mobile phase: dichloromethane→dichloromethane/methanol 50:1)
  6. customwere purified together)

Sources & evidence

ORD record
ord-27992ee92416415c8110d3cce6642e2c
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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