Hydrochloric Acid → 4-Ethyl-1-(4-fluoro-benzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid hydroxyamide

HRID 2377100Notes

Reaction equation

HRID 2377100 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH2:23][CH3:24])=[C:8]2[CH:14]=[CH:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:9]2=[CH:10][N:11]=1)=O)C.[OH-:25].[Na+].[NH2:27]O.Cl>CCO.O>[OH:25][NH:27][C:4]([C:6]1[C:7]([CH2:23][CH3:24])=[C:8]2[CH:14]=[CH:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:9]2=[CH:10][N:11]=1)=[O:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 598558221h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,4-ethyl-1-[(4-fluorophenyl)methyl]-,ethyl ester

Product 1

HCID 114933524-Ethyl-1-(4-fluoro-benzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid hydroxyamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 4-ethyl-1-(4-fluoro-benzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (57 mg, 0.175 mmol) in EtOH (2 mL), was added a 10% wt/wt solution of NaOH in water (0.5 mL) and a 50% wt/wt solution of hydroxylamine in water (1 mL). The reaction was stirred at room temperature for 18 hours, and then 1 N HCl was added till a pH of 7 was reached. The reaction was concentrated by rotary evaporation, and then purified by preparative HPLC to give the desired product. Yield 10 mg, 18%. 1H NMR (400 MHz, CDCl3) δ 1.36 (t, J=7.58 Hz, 3H), 3.47 (q, J=7.41 Hz, 2H), 5.38 (s, 2H), 6375 (d, J=3.28 Hz, 1H), 7.02 (m, 2H), 7.13 (m, 2H), 7.30 (m, 1H), 8.43 (s, 1H).

Workup

  1. concentrationThe reaction was concentrated by rotary evaporation
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-88601713bd6a4d08a3209b90ad6b0f10
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Reaction notes

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