Acetic Acid → HCID 11544190, compound

HRID 2377085Notes

Reaction equation

[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:17]([O:19]C)=O)[C:15]([OH:16])=[C:10]3[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:25][O:26][NH2:27].C(O)(=O)C>CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:17]([NH:27][O:26][CH3:25])=[O:19])[C:15]([OH:16])=[C:10]3[CH:9]=[CH:8]2)=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 63 °C

Procedure

To methyl 1-(4-fluorobenzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (0.6 g, 2 mmol) in methanol (10 ml) and water (1 ml) were added sodium hydroxide (0.56 g, 14 mmol) and O-methylhydroxylamine (0.668 g, 8 mmol). The resulting mixture was stirred for 28 hours at 63° C. Acetic acid (2 mL) was added to precipitate undesired byproduct, 1-(4-fluorobenzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid, which was removed by filtration. The filtrate was concentrated in under reduced pressure; the residue was dissolved in methanol and purified by preparative HPLC to provide the title compound as a white powder (0.035 g, 5.6% yield). 1H NMR (300 MHz, DMSO-d6) d ppm 3.76 (s, 3H) 5.60 (s, 2H) 6.75 (d, J=2.83 Hz, 1H) 7.17-7.24 (m, 2H) 7.32-7.39 (m, J=5.46 Hz, 2H) 7.76 (d, J=3.20 Hz, 1H) 8.47 (s, 1H) 12.08 (s, 1H) 12.89 (s, 1H). LC-MS (APCI, M+H+): 316.1. HPLC: 95% purity.

Workup

customto precipitate undesired byproduct, 1-(4-fluorobenzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid, which
customwas removed by filtration
concentrationThe filtrate was concentrated in under reduced pressure
dissolutionthe residue was dissolved in methanol
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-606971c6ed3746389f54430d098635c8
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468375B2

Reaction notes

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