HCID 7355185, compound → HCID 178489512, compound

HRID 1971459Notes

Reaction equation

HRID 1971459 reaction equation
[Cl:1][CH2:2][C:3](=[N:10]S(C1C=CC(C)=CC=1)(=O)=O)[N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[CH3:21][O:22][C:23]1[CH:36]=[CH:35][CH:34]=[CH:33][C:24]=1[CH2:25][NH:26][C:27](=[NH:32])[NH:28][C:29](N)=[S:30]>>[Cl-:1].[NH:32]=[C:27]([NH:28][C:29]1[S:30][CH2:2][C:3](=[N+:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)[N:10]=1)[NH:26][CH2:25][C:24]1[CH:33]=[CH:34][CH:35]=[CH:36][C:23]=1[O:22][CH3:21]

Participants

3

Reactant 2

HCID 7355185HCID 7355185, compoundHCID 178489514HCID 178489514, compound

Product 1

HCID 178489512HCID 178489512, compoundYield 8.3%

Procedure

Reaction of 100 mg (0.38 mmol) N-(2-chloro-1-piperidine-1-ylethylidene)-4-methylphenyl sulfonamide (preparation according to: Abdelaal, S.; Bauer, L. J. Het. Chem. 1988, 25 (6), 1849-1856) with 120 mg (0.38 mmol) N-[[(2-methoxybenzyl)amino](imino)-methyl]thiourea analogously to Example 3 yielded 12 mg of the desired product; ESI-MS [M+H+]=346.15. According to NMR, the compound exists as tautomeric mixture of 1-[2-({imino[(2-methoxybenzyl)amino]methyl}amino)-1,3-thiazole-4(5H)-ylidene]piperidine and N-(2-methoxybenzyl)-N′-(4-piperidine-1-yl-1,3-thiazole-2-yl)guanidine.

Sources & evidence

ORD record
ord-904b8fd09d97449083aad220cb75cd10
Source dataset
uspto-grants-2013_04
Patent number
US08431604B2

Reaction notes

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