Hydroxyamine hydrochloride → 1-(5-Chloro-thiophen-2-ylmethyl)-n-hydroxy-1h-pyrrolo[2,3-c]pyridine-5-carboxamide

HRID 2221474Notes

Reaction equation

HRID 2221474 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH2:7][N:8]2[C:12]3=[CH:13][N:14]=[C:15]([C:17]([O:19]CC)=O)[CH:16]=[C:11]3[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.N1C2=CN=C(C(OCC)=O)C=C2C=C1.ClC1SC(CCl)=CC=1.ClC1C(F)=C(C(F)=CC=1)CN1C2=CN=C(C(O)=O)C=C2C=C1.ClC1C(F)=C(C(F)=CC=1)CN1C2=CN=C(C([NH:82][OH:83])=O)C=C2C=C1.ClC1SC(CN2C3=CN=C(C(O)=O)C=C3C=C2)=CC=1.Cl.NO>>[Cl:1][C:2]1[S:6][C:5]([CH2:7][N:8]2[C:12]3=[CH:13][N:14]=[C:15]([C:17]([NH:82][OH:83])=[O:19])[CH:16]=[C:11]3[CH:10]=[CH:9]2)=[CH:4][CH:3]=1

Participants

8

Reactant 7

HCID 443297Hydroxyamine hydrochlorideHCID 5830792-Chloro-5-(chloromethyl)thiopheneHCID 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 21892218Ethyl 1-(5-chloro-thiophen-2-ylmethyl)-1h-pyrrolo[2,3-c]pyridine-5-carboxylate2×HCID 218922321-(5-Chloro-thiophen-2-ylmethyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic AcidHCID 445493881-(3-Chloro-2,6-difluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic Acid

Product 1

HCID 100408961-(5-Chloro-thiophen-2-ylmethyl)-n-hydroxy-1h-pyrrolo[2,3-c]pyridine-5-carboxamide

Procedure

Ethyl 1-(5-chloro-thiophen-2-ylmethyl)-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 with 2-chloro-5-(chloromethyl)-thiophene in a manner similar to step (a) of example 1. 1H NMR (CD3O D) δ: 8.89 (s, 1H), 8.48 (s, 1H), 7.72 (d, 1H, J=3.2 Hz), 6.99 (d, 1H, J=3.8 Hz)), 6.87 (d, 1H, J=4.8 Hz), 6.75(d, 1H, J=3.2 Hz), 5.73 (s, 2H), 4.46 (q, 2H, J=7.2 Hz), 1.46 (t, 3H, J=7.2 Hz). LCMS (API-ES, M+H+): 321.0. (b) 1-(5-Chloro-thiophen-2-yl methyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid. The title compound was prepared by hydrolysis of ethyl 1-(5-chloro-thiophen-2-ylmethyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate in a manner similar to step (b) of example 1. 1H NMR (DMSO-d6): δ: 9.05 (s, 1H), 8.34 (s, 1H), 7.88 (d, 1H, J=3.0 Hz), 7.12 (d, 1H, J=3.8 Hz), 7.01 (d, 1H, J=4.0 Hz), 6.75 (d, 1H, J=3.2 Hz), 5.78 (s, 2H). LCMS (API-ES, M+H+): 293.0. (c) 1-(5-Chloro-thiophen-2-yl methyl)-N-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxamide. The title compound was prepared by coupling of 1-(1-(5-Chloro-thiophen-2-ylmethyl)-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: 11.15 (s, 1H), 8.93 (s, 2H), 8.21 (s, 1H), 7.81 (d, 1H, J=2.1 Hz), 7.10 (d, 1H, J=3.6 Hz), 6.99 (d, 1H, J=2.8 Hz), 6.70 (d, 1H, J=3.0 Hz), 5.76 (s, 2H). LCMS (API-ES, M+H+): 308.0. HRMS calcd for C13H11N3O2SCI (M+H) 308.0261, found 308.0265. Anal. (C13H10CIN3O2S) C, H, N. HPLC: 100% purity.

Sources & evidence

ORD record
ord-2f9d738b3255445c9a0928bf7dfda245
Source dataset
uspto-grants-2008_05
Patent number
US07368571B2

Reaction notes

Loading…