4-[(E)-2-ethoxyvinyl]-1-[(4-fluorophenyl)methyl]pyrrolo[2,3-c]pyridine-5-carbohydroxamic acid → 3-(4-Fluorobenzyl)-7-hydroxy-3,7-dihydro-6H-pyrrolo[2,3-c]-1,7-naphthyridin-6-one

HRID 640700Notes

Reaction equation

HRID 640700 reaction equation
C(O/[CH:4]=[CH:5]/[C:6]1[C:11]([C:12]([NH:14][OH:15])=[O:13])=[N:10][CH:9]=[C:8]2[N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH:17]=[CH:18][C:7]=12)C>CO.Cl>[F:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][N:16]2[C:8]3[CH:9]=[N:10][C:11]4[C:12](=[O:13])[N:14]([OH:15])[CH:4]=[CH:5][C:6]=4[C:7]=3[CH:18]=[CH:17]2)=[CH:25][CH:24]=1

Participants

4

Reactant 1

HCID 159570544-[(E)-2-ethoxyvinyl]-1-[(4-fluorophenyl)methyl]pyrrolo[2,3-c]pyridine-5-carbohydroxamic acid

Product 1

HCID 116165313-(4-Fluorobenzyl)-7-hydroxy-3,7-dihydro-6H-pyrrolo[2,3-c]-1,7-naphthyridin-6-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 4-[(E)-2-ethoxyvinyl]-1-(4-fluorobenzyl)-N-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxamide (100 mg, 0.28 mmol) in methanol (10 mL) and hydrochloric acid (37 w %, 1 mL) was refluxed for 16 hours. It was quenched with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated and purified by pre-HPLC to provide the title compound as white powder. 1H NMR (DMSO-d6) δ; 11.50 (s, 1H), 9.04 (s, 1H), 7.88 (d, 1H, J=3.0 Hz), 7.84 (d, 1H, J=7.5 Hz), 7.13-7.19 (m, 3H), 6.93 (d, 1H, J=7.5 Hz), 5.65 (s, 2H). MS (APCl, M+H+): 310.1. HRMS calcd for C17H13N3O2F1 (M+H+) 310.0992, found 310.0991. HPLC: 94.3% purity.

Workup

  1. customIt was quenched with saturated sodium bicarbonate solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by pre-HPLC

Sources & evidence

ORD record
ord-52d19200558b429593a4402ad22791b5
Source dataset
uspto-grants-2010_04
Patent number
US07692014B2

Reaction notes

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