1-(5-Chloro-4-nitrothiophen-2-yl)-3-(1-methylpiperidin-4-yl)urea → 1-(5-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophen-2-yl)-3-(1-methylpiperidin-4-yl)urea

HRID 1192278Notes

Reaction equation

HRID 1192278 reaction equation
Cl[C:2]1[S:6][C:5]([NH:7][C:8]([NH:10][CH:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[O:9])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].[Na].[Cl:22][C:23]1[CH:24]=[N:25][CH:26]=[C:27]([Cl:30])[C:28]=1[SH:29]>>[Cl:22][C:23]1[CH:24]=[N:25][CH:26]=[C:27]([Cl:30])[C:28]=1[S:29][C:2]1[S:6][C:5]([NH:7][C:8]([NH:10][CH:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[O:9])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19]

Participants

3

Reactant 2

HCID 602075081-(5-Chloro-4-nitrothiophen-2-yl)-3-(1-methylpiperidin-4-yl)ureaHCID 178527724HCID 178527724, compound

Product 1

HCID 602075091-(5-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophen-2-yl)-3-(1-methylpiperidin-4-yl)urea

Procedure

Prepared according to the procedure described for step A of example 18 from 1-(5-chloro-4-nitrothiophen-2-yl)-3-(1-methylpiperidin-4-yl)urea (100 mg, 0.31 mmol) and 3,5-dichloropyridine-4-thiol sodium salt (62 mg, 0.35 mmol). The title compound was obtained as a white solid (120 mg, 85% yield). 1H NMR (400 MHz, d6-DMSO) δ: 10.01 (1H, m), 8.92 (2H, m), 6.91 (1H, m), 3.43 (2H, m), 2.87 (2H, m), 2.33 (3H, m), 1.91 (1H, m), 1.74 (2H, m), 1.46 (2H, m). MS m/z: 459.94, 461.94 [M+H]+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-07c81d8f50e24e5d9543b38e978fc44b
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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