Hydroxyamine hydrochloride → 1-(3-chloro-2-fluorobenzyl)-N-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxamide

HRID 2221475Notes

Reaction equation

HRID 2221475 reaction equation
ClC1C(F)=C(C=CC=1)CN1C2=CN=C(C(OCC)=O)C=C2C=C1.N1C2=CN=C(C(OCC)=O)C=C2C=C1.ClC1C(F)=C(C=CC=1)CBr.ClC1C(F)=C(C(F)=CC=1)CN1C2=CN=C(C(O)=O)C=C2C=C1.[Cl:70][C:71]1[C:72]([F:92])=[C:73]([C:88](F)=[CH:89][CH:90]=1)[CH2:74][N:75]1[C:79]2=[CH:80][N:81]=[C:82]([C:84]([NH:86][OH:87])=[O:85])[CH:83]=[C:78]2[CH:77]=[CH:76]1.ClC1C(F)=C(C=CC=1)CN1C2=CN=C(C(O)=O)C=C2C=C1.Cl.NO>>[Cl:70][C:71]1[C:72]([F:92])=[C:73]([CH:88]=[CH:89][CH:90]=1)[CH2:74][N:75]1[C:79]2=[CH:80][N:81]=[C:82]([C:84]([NH:86][OH:87])=[O:85])[CH:83]=[C:78]2[CH:77]=[CH:76]1

Participants

8

Reactant 7

HCID 443297Hydroxyamine hydrochlorideHCID 5228271-(Bromomethyl)-3-chloro-2-fluorobenzeneHCID 100656851-[(3-Chloro-2,6-difluoro-phenyl)methyl]pyrrolo[2,3-c]pyridine-5-carbohydroxamic acidHCID 10702827ethyl 1H-pyrrolo[2,3-c]pyridine-5-carboxylateHCID 218922001-(3-chloro-2-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acidHCID 21892239Ethyl 1-(3-chloro-2-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate2×HCID 445493881-(3-Chloro-2,6-difluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic Acid

Product 1

HCID 103586011-(3-chloro-2-fluorobenzyl)-N-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxamide

Procedure

Ethyl 1-(3-chloro-2-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate. The title compound was prepared by alkylation of ethyl 1H-pyrrolo[2,3-c]pyridine-5-carboxylate and 3-chloro-2-fluoro-benzyl bromide in a manner similar to step (a) of example 1. 1H NMR (CDCl3) δ: 9.05 (s, 1H), 8.50 (s, 1H), 7.55 (d, 1H, J=3.0 Hz), 7.40 (m, 1H), 7.00 (m, 2H), 6.80 (d, 1H, J=3.0 Hz), 5.55 (s, 2H), 4.50 (q, 2H, J=7.0 Hz), 1.50 (t, 3H, J=7.0 Hz). LCMS (API-ES, M+H+): 333.0. (b) 1-(3-Chloro-2-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid. The title compound was prepared by hydrolysis of ethyl 1-(3-chloro-2-fluoro-benzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate in a manner similar to step (b) of example 1. 1H NMR (DMSO-d6): δ: 8.96 (s, 1H), 8.35 (s, 1H), 7.84 (d, 1H, J=3.0 Hz), 7.56 (t, 1H, J=7.4 Hz), 7.19 (t, 1H, J=7.9 Hz), 7.09 (t, 1H, J=7.3 Hz), 5.75 (s, 2H). LCMS (API-ES, M+H+): 305.0. (c) 1-(3-Chloro-2-fluorobenzyl)-N-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxamide. The title compound was prepared by coupling of 1-(3-chloro-2-fluoro-benzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid with hydroxylamine hydrochloride in a manner similar to step (c) of example 1. 1H NMR (DMSO-d6) δ: 11.16 (s, 1H), 8.95 (s, 1H), 8.85 (s, 1H), 8.23 (s, 1H), 7.79 (d, 1H, J=2.8 Hz), 7.55 (t,1H, J=7.5 Hz), 7.19 (t, 1H, J=7.5 Hz), 7.10 (t, 1H, J=7.5 Hz), 6.73 (d, 1H, J=3.0 Hz), 5.74 (s, 2H). LCMS (API-ES, M+H+): 320.0. HRMS calcd for C15H12CIFN3O2 (M+H) 320.0602, found 320.06045. HPLC: 100% purity.

Sources & evidence

ORD record
ord-52dc366e74134493a494f88e4b93c3d7
Source dataset
uspto-grants-2008_05
Patent number
US07368571B2

Reaction notes

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