Acetic Acid → 1-(4-Fluorobenzyl)-N-hydroxy-4-(3-hydroxypropyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxamide

HRID 2377093Notes

Reaction equation

HRID 2377093 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:20](OCC)=[O:21])[C:15]([CH2:16][CH2:17][CH2:18][OH:19])=[C:10]3[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.[OH-:27].[Na+].[NH2:29]O.C(O)(=O)C>CO>[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:20]([NH:29][OH:27])=[O:21])[C:15]([CH2:16][CH2:17][CH2:18][OH:19])=[C:10]3[CH:9]=[CH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 686660171h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,1-[(4-fluorophenyl)methyl]-4-(3-hydroxypropyl)-,ethyl ester

Product 1

HCID 116458691-(4-Fluorobenzyl)-N-hydroxy-4-(3-hydroxypropyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxamideYield 19.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 1-(4-fluorobenzyl)-4-(3-hydroxypropyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (22 mg, 0.06 mmol) in MeOH (3 mL) was added sodium hydroxide (15 mg, 0.38 mmol) and hydroxylamine (50 wt. % in water) (82.5 mg, 1.25 mmol). The resulting mixture was stirred for 18 h at room temperature. The mixture was neutralized by acetic acid and concentrated. The title compound was purified by preparative HPLC to provide the title compound as a white powder (4 mg, 19% yield). 1H NMR (300 MHz, MeOH) δ ppm 8.53 (s, 1H) 7.63 (d, J=3.20 Hz, 1H) 7.20-7.27 (m, J=8.57, 5.37 Hz, 2H) 7.05 (t, J=8.76 Hz, 2H) 6.81 (d, J=2.83 Hz, 1H) 5.52 (s, 2H) 3.60 (t, J=6.31 Hz, 2H) 1.90-2.04 (m, 4H). LC-MS (APCI, M+H+): 344.2. HPLC: 90% purity.

Workup

  1. concentrationconcentrated
  2. customThe title compound was purified by preparative HPLC

Sources & evidence

ORD record
ord-6a143d1ddab444baa1faab62cf982b70
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Reaction notes

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