Hydrochloric Acid → 4-carbamoyl-2-(3-fluoro-4-methoxyphenyl)-5H-pyrido[3,2-b]indole-7-carboxylic acid

HRID 2410743Notes

Reaction equation

HRID 2410743 reaction equation
[C:1]([C:4]1[C:9]2[NH:10][C:11]3[CH:12]=[C:13]([C:17]([O:19]C)=[O:18])[CH:14]=[CH:15][C:16]=3[C:8]=2[N:7]=[C:6]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([F:29])[CH:22]=2)[CH:5]=1)(=[O:3])[NH2:2].CO.[OH-].[Na+].Cl>C1COCC1>[C:1]([C:4]1[C:9]2[NH:10][C:11]3[CH:12]=[C:13]([C:17]([OH:19])=[O:18])[CH:14]=[CH:15][C:16]=3[C:8]=2[N:7]=[C:6]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([F:29])[CH:22]=2)[CH:5]=1)(=[O:3])[NH2:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 66604472methyl 4-carbamoyl-2-(3-fluoro-4-methoxyphenyl)-5H-pyrido[3,2-b]indole-7-carboxylate

Product 1

HCID 666054684-carbamoyl-2-(3-fluoro-4-methoxyphenyl)-5H-pyrido[3,2-b]indole-7-carboxylic acidYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-carbamoyl-2-(3-fluoro-4-methoxyphenyl)-5H-pyrido[3,2-b]indole-7-carboxylate (75 mg, 0.19 mmol) in a mixture of THF (3 ml), MeOH (1 ml) and 1 N aqueous sodium hydroxide (3.0 ml, 3.0 mmol) was stirred at room temperature for 24 hr. This was neutralized with 1 N aqueous HCl and the organic solvents were removed on the rotary evaporator. The residue was dissolved in water and acidified to about pH 3 with 1 N aqueous HCl. The mixture was chilled in an ice bath and the precipitate was collected by filtration and dried to give 4-carbamoyl-2-(3-fluoro-4-methoxyphenyl)-5H-pyrido[3,2-b]indole-7-carboxylic acid (70 mg) as a yellow solid. MS (ESI) m/z 380.0 (M+H). 1H NMR (DMSO-d6) δ ppm 11.87 (1H, s), 8.64 (1H, br. s.), 8.50 (1H, s), 8.41 (1H, s), 8.36 (1H, d, J=7.93 Hz), 8.11-8.21 (2H, m), 7.96(1H, br. s.), 7.87 (1H, d, J=8.24 Hz), 7.36 (1H, t, J=8.85 Hz), 3.95 (3H, s).

Workup

  1. customthe organic solvents were removed on the rotary evaporator
  2. dissolutionThe residue was dissolved in water
  3. temperatureThe mixture was chilled in an ice bath
  4. filtrationthe precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-69567a94ddc845b0afaa976e9b13ad99
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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