5-(Aminomethyl)-2-chloropyridine → HCID 60207390, compound

HRID 1192174Notes

Reaction equation

HRID 1192174 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([OH:16])=O)=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18].[Cl:21][C:22]1[N:27]=[CH:26][C:25]([CH2:28][NH2:29])=[CH:24][CH:23]=1>>[Cl:21][C:22]1[N:27]=[CH:26][C:25]([CH2:28][NH:29][C:14]([C:12]2[S:13][C:9]([S:8][C:7]3[C:6]([Cl:20])=[CH:5][N:4]=[CH:3][C:2]=3[Cl:1])=[C:10]([N+:17]([O-:19])=[O:18])[CH:11]=2)=[O:16])=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 70209275-(Aminomethyl)-2-chloropyridineHCID 602073175-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carboxylic acid

Product 1

HCID 60207390HCID 60207390, compound

Procedure

Prepared according to the procedure described for example 50 from 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carboxylic acid (1.0 g, 2.85 mmol) and (6-chloropyridin-3-yl)methylamine (488 mg, 3.42 mmol). The title compound was obtained as a solid (500 mg, 37% yield). 1H NMR (400 MHz, d6-DMSO) δ: 9.43 (1H, m), 9.00 (2H, s), 8.44 (1H, s), 8.34 (1H, s), 7.77 (1H, dd), 7.49 (1H, dd), 4.23 (2H, m). MS m/z: 473.05, 475.03 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-5297fe8b8eff45eb96aadd3ccafe1fcc
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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