Hydrochloric Acid → HCID 18663762, compound

HRID 1956774Notes

Reaction equation

HRID 1956774 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:4]=1[C:12]1[C:21]([CH3:22])=[C:20]([C:23]([O:25]C)=[O:24])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:27][N:28]3[C:32]4=[N:33][CH:34]=[CH:35][CH:36]=[C:31]4[N:30]=[C:29]3[CH2:37][CH2:38][CH2:39][CH3:40])[CH:18]=2)[N:13]=1.[OH-].[Na+].Cl>CO>[CH3:1][O:2][C:3]1[C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:4]=1[C:12]1[C:21]([CH3:22])=[C:20]([C:23]([OH:25])=[O:24])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:27][N:28]3[C:32]4=[N:33][CH:34]=[CH:35][CH:36]=[C:31]4[N:30]=[C:29]3[CH2:37][CH2:38][CH2:39][CH3:40])[CH:18]=2)[N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18663767HCID 18663767, compound

Product 1

HCID 18663762HCID 18663762, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In 35 ml of methanol were dissolved 3.6 g (6.9 mmol) of methyl 2-(2-methoxycarboxyphenyl)-3-methyl-6-[(2-butyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]-4-quinolinecarboxylate obtained in the method described in Example 36. Then, 14 ml of a 0.5N aqueous solution of sodium hydroxide were added thereto and the mixture was stirred at room temperature for 16 hours. After the reaction mixture was neutralized with 1N hydrochloric acid, methanol was distilled off and 35 ml of water were added to the residue. The mixture was extracted with 30 ml of methylene chloride and the aqueous layer was acidified with 2N hydrochloric acid under stirring. The resulting precipitate was collected by filtration, washed with water and dried to give 1.8 g of 2-(2-methoxycarboxyphenyl)-3-methyl-6-[(2-butyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]-4-quinolinecarboxylic acid. NMR (270 MHz, CDCl3) δ 8.3 (m,1H); 8.0-8.1 (m,3H); 7.79 (d,J=7.8Hz,1H); 7.1-7.6 (m,5H); 5.71 (s,2H); 3.5 (s,3H); 2.87 (t,J=7.8Hz,2H); 2.6 (s,3H); 1.80-1.88 (m,2H); 1.4-1.48 (m,2H); 0.92 (t,J=7.3Hz,3H).

Workup

  1. customobtained in the method
  2. distillationwas distilled off
  3. addition35 ml of water were added to the residue
  4. extractionThe mixture was extracted with 30 ml of methylene chloride
  5. stirringunder stirring
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-2ba3998d35a845689fc6f7099a555a00
Source dataset
uspto-grants-1998_07
Patent number
US05780634

Reaction notes

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