Sodium Hydroxide → 1-(5-Ethoxy-[1,2,3]thiadiazol-4-ylmethyl)-N-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxamide

HRID 2221476Notes

Reaction equation

HRID 2221476 reaction equation
ClC1SN=NC=1CN1C2=CN=C(C(OCC)=O)C=C2C=C1.N1C2=CN=C(C(OCC)=O)C=C2C=C1.ClC1SN=NC=1CCl.[CH2:44]([O:46][C:47]1[S:51][N:50]=[N:49][C:48]=1[CH2:52][N:53]1[C:57]2=[CH:58][N:59]=[C:60]([C:62]([OH:64])=O)[CH:61]=[C:56]2[CH:55]=[CH:54]1)[CH3:45].[OH-].[Na+].ClC1C(F)=C(C(F)=CC=1)CN1C2=CN=C(C([NH:83][OH:84])=O)C=C2C=C1.Cl.NO>C(O)C>[CH2:44]([O:46][C:47]1[S:51][N:50]=[N:49][C:48]=1[CH2:52][N:53]1[C:57]2=[CH:58][N:59]=[C:60]([C:62]([NH:83][OH:84])=[O:64])[CH:61]=[C:56]2[CH:55]=[CH:54]1)[CH3:45]

Participants

9

Reactant 7

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 27974905-Chloro-4-(chloromethyl)-1,2,3-thiadiazoleHCID 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 218922201-(5-Ethoxy-[1,2,3]thiadiazol-4-ylmethyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid2×HCID 21892241Ethyl 1-(5-chloro-[1,2,3]thiadiazol-4-ylmethyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate2×

Product 1

HCID 99960571-(5-Ethoxy-[1,2,3]thiadiazol-4-ylmethyl)-N-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-(5-chloro-[1,2,3]thiadiazol-4-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 and 5-chloro-4-chloromethyl-[1,2,3]thiadiazole in a manner similar to step (a) of example 1. 1H NMR (DMSO-d6) δ: 8.99 (s, 1H), 8.36 (s, 1H), 7.85 (d, 1H, J=3.0 Hz), 6.75 (d, 1H, J=3.0 Hz), 6.04 (s, 2H), 4.32 (q, 2H, J=7.0 Hz), 1.32 (t, 3H, J=7.0 Hz). LCMS (API-ES, M+H+): 323.0. (b) 1-(5-Ethoxy-[1,2,3]thiadiazol-4-ylmethyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid. The title compound was prepared by hydrolysis of ethyl 1-(5-chloro-[1,2,3]thiadiazol-4-ylmethyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate in a manner similar to step (b) of example 1 using sodium hydroxide as base and anhydrous ethanol as solvent. 1H NMR (DMSO-d6): δ: 9.01 (s, 1H), 8.35 (s, 1H), 7.85 (d, 1H, J=3.0 Hz), 6.75 (d, 1H, J=3.0 Hz), 5.86 (s, 2H), 4.36 (q, 2H, J=6.8 Hz), 1.42 (t, 3H, J=6.8 Hz). LCMS (API-ES, M+H+): 305.0. (c) 1-(5-Ethoxy-[1,2,3]thiadiazol-4-ylmethyl)-N-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxamide. The title compound was prepared by coupling of 1-(5-ethoxy-[1,2,3]thiadiazol-4-ylmethyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid and hydroxylamine hydrochloride in a manner similar to step (c) of example 1. 1H NMR (DMSO-d6) 6; 11.15 (s, 1H), 8.88 (s, 2H), 8.19 (s, 1H), 7.73 (d, 1H, J=3.0 Hz), 6.66 (d, 1H, J=3.0 Hz), 5.81 (s, 2H), 4.32 (q, 2H, J=6.8 Hz), 1.39 (t, 3H, J=6.9 Hz). LCMS (APCI, M+H+): 320.1. HRMS calcd for C13H14N5O3S (M+H) 320.0817, found 320.0823. HPLC: 100% purity.

Sources & evidence

ORD record
ord-9f0b1674fce249f982118131e77ec694
Source dataset
uspto-grants-2008_05
Patent number
US07368571B2

Reaction notes

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