Hydrochloric Acid → 2-[N-(4-amidinophenyl)aminomethyl]benzothiazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-methoxycarbonylethyl)amide dihydrochloride

HRID 2288342Notes

Reaction equation

HRID 2288342 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])[C:8]([C:10]1[CH:11]=[CH:12][C:13]2[S:17][C:16]([CH2:18][NH:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=3)=[N:15][C:14]=2[CH:28]=1)=[O:9].[ClH:35].CO.C(=O)([O-])[O-].[NH4+:42].[NH4+]>C(O)(=O)C.C(Cl)Cl.C(O)C>[ClH:35].[ClH:35].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])[C:8]([C:10]1[CH:11]=[CH:12][C:13]2[S:17][C:16]([CH2:18][NH:19][C:20]3[CH:25]=[CH:24][C:23]([C:26](=[NH:42])[NH2:27])=[CH:22][CH:21]=3)=[N:15][C:14]=2[CH:28]=1)=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 517111Ammonium CarbonateHCID 184124972-[N-(4-cyanophenyl)aminomethyl]benzothiazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-methoxycarbonylethyl)amide

Product 1

HCID 184126362-[N-(4-amidinophenyl)aminomethyl]benzothiazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-methoxycarbonylethyl)amide dihydrochlorideYield 68%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 9 from 2-[N-(4-cyanophenyl)-aminomethyl]benzothiazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-methoxycarbonylethyl)-amide, methanolic hydrochloric acid, methanol and ammonium carbonate. Yield: 68% of theory, C25H24N6O3S (488.57) Rf value: 0.13 (silica gel; methylene chloride/ethanol=4:1+a few drops of acetic acid) EKA mass spectrum: (M+H)+ =489

Sources & evidence

ORD record
ord-ecdfad7505f84476ab96f7572e0c9cc4
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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