Benzenesulfonyl chloride → HCID 178491356, compound

HRID 1971474Notes

Reaction equation

HRID 1971474 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[C:4]=1[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][C:12]2[CH2:13][NH:14][CH2:15][CH2:16][C:17]=2[N:18]=1)=[NH:8].[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[C:4]=1[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][C:12]2[CH2:13][N:14]([S:31]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)(=[O:33])=[O:32])[CH2:15][CH2:16][C:17]=2[N:18]=1)=[NH:8]

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 178491353HCID 178491353, compound

Product 1

HCID 178491356HCID 178491356, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Reaction of 30 mg N-(2,6-dimethoxybenzyl)-N′-(4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-yl)guanidine (0.09 mmol, Example 221.3) with 18 mg phenylsulfonic acid chloride and 40 mg polymer-bound DMAP (Argonaut; 1.06 mmol/g) in 5 ml dichloromethane followed by chromatographic purification (dichloromethane/methanol 2-4%) yielded 15 mg of the target product; ESI-MS [M+H+]=488.15.

Workup

  1. customfollowed by chromatographic purification (dichloromethane/methanol 2-4%)

Sources & evidence

ORD record
ord-7bdae9bc486f4c2a9c0ec2aeb16c0066
Source dataset
uspto-grants-2013_04
Patent number
US08431604B2

Reaction notes

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