22661-87-6

Usage

Uses

Used in Pharmaceutical Industry:
Methylguanidine hydrochloride is used as an inhibitor for [application type] due to its ability to inhibit trypsin catalysis and metabolism of certain hepatic drugs. This makes it a valuable compound in the development of drugs targeting specific metabolic pathways and enzyme interactions.
Used in Research and Development:
In the field of research and development, Methylguanidine hydrochloride serves as a crucial tool for studying the mechanisms of trypsin inhibition and the role of cytochrome P450 protein in drug metabolism. Its use in this context aids in understanding the complex interactions between enzymes and their substrates, potentially leading to the discovery of novel therapeutic strategies.
Used in Diagnostic Applications:
Methylguanidine hydrochloride can be employed as a diagnostic agent for [application reason] in the assessment of liver function and the activity of cytochrome P450 proteins. Its inhibitory properties allow for the evaluation of enzyme activity levels, which can be indicative of various liver-related conditions and drug metabolism efficiency.

InChI:InChI=1/C2H7N3.ClH/c1-2(3)5-4;/h5H,1,3-4H2;1H

Synthetic route

methylamine hydrochloride (593-51-1) + N-Cyanoguanidine (127099-85-8, 780722-26-1) → 1-methylguanidine hydrochloride (22661-87-6)

Conditions	Yield
	64%
In methanol at 180℃; for 3h;

(E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one (67751-23-9) + 1-methylguanidine hydrochloride (22661-87-6) → 4-(dimethoxymethyl)-N-methylpyrimidin-2-amine (180869-38-9)

Conditions	Yield
With sodium In ethanol for 3h; Heating / reflux;	100%
With sodium hydroxide

1-methylguanidine hydrochloride (22661-87-6) + 5-Dimethylamino-3-oxo-4-penten-2-one-3-dimethylketal (106157-94-2) → [4-(1,1-dimethoxy-ethyl)-pyrimidin-2-yl]-methyl-amine

Conditions	Yield
With ethanol; sodium for 4h; Heating / reflux;	100%
With sodium In ethanol for 4 - 6.5h; Heating / reflux;	100%
With sodium In ethanol for 4h; Heating / reflux;	100%

1-(3-bromo-4-fluorophenyl)-2-(4-methoxy-3-methylphenyl)ethane-1,2-dione (1202708-26-6) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-5-(3-bromo-4-fluorophenyl)-5-(4-methoxy-3-methylphenyl)-3-methyl-3,5-dihydro-4H-imidazol-4-one (872041-81-1)

Conditions	Yield
With sodium carbonate In 1,4-dioxane; ethanol; water at 70℃; for 5h;	99%
Stage #1: 1-(3-bromo-4-fluorophenyl)-2-(4-methoxy-3-methylphenyl)ethane-1,2-dione; 1-methylguanidine hydrochloride In 1,4-dioxane; ethanol at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With sodium carbonate In 1,4-dioxane; ethanol; water at 85℃; for 0.75h; Inert atmosphere;	90%

1-(3-bromophenyl)-2-(4-(difluoromethoxy)-3-methylphenyl)ethane-1,2-dione (1062613-90-4) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-5-(3-bromophenyl)-5-(4-(difluoromethoxy)-3-methylphenyl)-3-methyl-3,5-dihydro-4H-imidazol-4-one (1062604-64-1)

Conditions	Yield
With sodium carbonate In isopropyl alcohol at 80℃; for 2h;	98.3%

1-(3-cyclopropyl-4-(difluoromethoxy)phenyl)-2-(3-(5-fluoropent-1-ynyl)phenyl)ethane-1,2-dione (1062617-07-5) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-4-(3-cyclopropyl-4-(difluoromethoxy)phenyl)-4-(3-(5-fluoropent-1-ynyl)phenyl)-1-methyl-1H-imidazol-5(4H)-one (1062609-15-7)

Conditions	Yield
With sodium carbonate In isopropyl alcohol at 86℃; for 16h;	98%

1-methylguanidine hydrochloride (22661-87-6) + 1-phenyl-5-(1-benzoyl-2-dimethylaminovinyl)-1H-tetrazole → Methyl-[4-phenyl-5-(1-phenyl-1H-tetrazol-5-yl)-pyrimidin-2-yl]-amine

Conditions	Yield
With sodium ethanolate In ethanol for 2h; Heating;	97%

1-methylguanidine hydrochloride (22661-87-6) + 5-(2-Dimethylamino-1-trifluoracetyl-vinyl)-1-phenyl-1H-tetrazol → Methyl-[5-(1-phenyl-1H-tetrazol-5-yl)-4-trifluoromethyl-pyrimidin-2-yl]-amine

Conditions	Yield
With sodium ethanolate In ethanol for 2h; Heating;	96%

1-[4-(difluoromethoxy)phenyl]-2-phenylethane-1,2-dione + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-5-[4-(difluoromethoxy)phenyl]-3-methyl-5-phenyl-3,5-dihydro-4H-imidazol-4-one

Conditions	Yield
With sodium carbonate In 1,4-dioxane; ethanol; water at 95℃; for 3h;	94%
With sodium carbonate In 1,4-dioxane; ethanol; water at 95℃; for 3h;	94%

3-bromo-4'-methoxy-benzil (860599-82-2) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-5-(3-bromo-phenyl)-5-(4-methoxy-phenyl)-3-methyl-3,5-dihydro-4H-imidazol-4-one (937374-15-7)

Conditions	Yield
Stage #1: 3-bromo-4'-methoxy-benzil; 1-methylguanidine hydrochloride In 1,4-dioxane; ethanol; water; acetonitrile at 20℃; for 0.25h; Stage #2: With sodium carbonate In 1,4-dioxane; ethanol; water at 85℃; for 0.75h;	94%

1-methylguanidine hydrochloride (22661-87-6) + methyl 1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)imidazole-4,5-dicarboxylate (66657-09-8) → 4,5-dihydro-8H-6-(N-methyl)amino-1-(β-D-ribofuranosyl)imidazo[4,5-e][1,3]diazepine-4,8-dione

Conditions	Yield
Stage #1: 1-methylguanidine hydrochloride With sodium methylate In methanol for 0.5h; Stage #2: methyl 1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)imidazole-4,5-dicarboxylate With sodium methylate In methanol at 20℃;	93%

1-(4-Fluorophenyl)-3-isopropylpropan-1,3-dione (114433-94-2) + 1-methylguanidine hydrochloride (22661-87-6) → 4-(4-fluoro phenyl)-6-isopropyl-N-methyl-pyrimidin-2-amine (1031246-31-7)

Conditions	Yield
With potassium hydroxide In isopropyl alcohol Temperature; Reflux;	93%
With potassium hydroxide In acetone Temperature; Concentration; Reflux;	93%
With potassium hydroxide In isopropyl alcohol Solvent; Reflux;	93%
Stage #1: 1-methylguanidine hydrochloride With sodium In isopropyl alcohol at 82℃; for 2.5h; Stage #2: 1-(4-Fluorophenyl)-3-isopropylpropan-1,3-dione In isopropyl alcohol at 82℃; for 11h;	65%
Stage #1: 1-methylguanidine hydrochloride With sodium isopropylate In isopropyl alcohol at 82℃; for 2.5h; Stage #2: 1-(4-Fluorophenyl)-3-isopropylpropan-1,3-dione In isopropyl alcohol at 82℃; for 11h;	65%

3-[2-(4-Difluoromethoxy-phenyl)-2-oxo-acetyl]-benzaldehyde + 1-methylguanidine hydrochloride (22661-87-6) → 3-{2-amino-4-[4-(difluoromethoxy)phenyl]-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl}benzaldehyde (931429-87-7)

Conditions	Yield
With sodium carbonate In isopropyl alcohol at 86℃; for 15.5h;	93%

2-Acetyl-7-methoxytropone (72030-45-6) + 1-methylguanidine hydrochloride (22661-87-6) → 4-acetyl-2-methylaminocycloheptimidazole (143769-47-5)

Conditions	Yield
In ethanol for 3h; Heating;	91%

1-(2-chloropyridin-3-yl)-3-dimethylaminopropenone (166196-84-5) + 1-methylguanidine hydrochloride (22661-87-6) → 4-(2-chloropyridin-3-yl)-N-methylpyrimidin-2-amine (870221-22-0)

Conditions	Yield
Stage #1: 1-methylguanidine hydrochloride With sodium methylate In methanol for 0.5h; Stage #2: 1-(2-chloropyridin-3-yl)-3-dimethylaminopropenone In methanol at 50℃; for 23h;	90%

chloro(2,2':6',2''-terpyridine)platinum(II) chloride dihydrate + 1-methylguanidine hydrochloride (22661-87-6) → {(Pt(2,2':6',2''-terpyridine))2(methylguanidine)}Cl4 + {Pt(2,2':6',2''-terpyridine)(methylguanidine)}Cl2

Conditions	Yield
In water Pt-complex, the guanidine in H2O kept at 80°C, 5d, pH adjusted to ca 8.0 with NaOH; chromy. (CM52 cation exchanger; elution: potassium phosphate buffer pH7.0 at 4°C);	A 90% B 10%

(E)-1-(2-(4-(tert-b utyl)phenyl)-4-methylthiazol-5-yl)-3-(dimethylamino)prop-2-en-1-one + 1-methylguanidine hydrochloride (22661-87-6) → 4-(2-(4-(tert-butyl)phenyl)-4-methylthiazol-5-yl)-N-methylpyrimidin-2-amine

Conditions	Yield
With potassium carbonate In ethanol for 8h; Reflux;	89%

1-(3-cyclopropyl-4-(difluoromethoxy)phenyl)-2-(3-(4-methoxybut-1-ynyl)phenyl)ethane-1,2-dione (1062616-96-9) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-4-(3-cyclopropyl-4-(difluoromethoxy)phenyl)-4-(3-(4-methoxybut-1-ynyl)phenyl)-1-methyl-1H-imidazol-5(4H)-one (1062608-84-7)

Conditions	Yield
With sodium carbonate In isopropyl alcohol at 86℃; for 16h;	88%

1-(4-(difluoromethoxy)-3-methylphenyl)-2-phenylethane-1,2-dione (1062613-70-0) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-5-[4-(difluoromethoxy)-3-methylphenyl]-3-methyl-5-phenyl-3,5-dihydro-4H-imidazol-4-one (1062604-38-9)

Conditions	Yield
With sodium carbonate In ethanol at 80℃;	86%

N-Boc-N-methyl-dehydroalanine methyl ester (56776-34-2) + 1-methylguanidine hydrochloride (22661-87-6) → (2-amino-1-methyl-4-oxo-1,4,5,6-tetrahydro-pyrimidin-5-yl)-methyl-carbamic acid tert-butyl ester (601507-04-4)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃;	85%

1-(4-Difluoromethoxy-phenyl)-2-[3-(1-fluoro-pent-4-enyl)-phenyl]-ethane-1,2-dione (1065168-04-8) + 1-methylguanidine hydrochloride (22661-87-6) → 2-Amino-5-(4-difluoromethoxy-phenyl)-5-[3-(1-fluoro-pent-4-enyl)-phenyl]-3-methyl-3,5-dihydro-imidazol-4-one (1065165-18-5)

Conditions	Yield
With sodium carbonate In 1,4-dioxane; ethanol; water at 95℃; for 3h;	85%

1-methylguanidine hydrochloride (22661-87-6) + 1,1,5,5-tetraethyl-3-fluoro-1,5-diazapentadienium iodide → (5-Fluoro-pyrimidin-2-yl)-methyl-amine

Conditions	Yield
With sodium methylate In methanol; acetonitrile at 70 - 75℃; for 3h;	84%

1-(4-Difluoromethoxy-phenyl)-2-{3-[3-(2-fluoro-ethyl)-cyclobutyl]-phenyl}-ethane-1,2-dione (1065168-72-0) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-5-[4-(difluoromethoxy)phenyl]-5-{3-[3-(2-fluoroethyl)cyclobutyl]phenyl}-3-methyl-3,5-dihydro-4H-imidazol-4-one (1065166-21-3)

Conditions	Yield
With sodium carbonate In ethanol at 89℃; for 16h;	84%

(E)-3-(dimethylamino)-2-(3-nitrophenoxy)prop-2-enenitrile + 1-methylguanidine hydrochloride (22661-87-6) → N2-methyl-5-(3-nitrophenoxy)pyrimidine-2,4-diamine

Conditions	Yield
With potassium carbonate In butan-1-ol at 100℃; for 2h;	84%

1-(3-bromo-phenyl)-2-(3-cyclopropyl-4-difluoromethoxy-phenyl)-ethane-1,2-dione (1062616-71-0) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-5-(3-bromo-phenyl)-5-(3-cyclopropyl-4-difluoromethoxy-phenyl)-3-methyl-3,5-dihydro-imidazol-4-one (1062608-28-9)

Conditions	Yield
With sodium carbonate In isopropyl alcohol at 86℃; for 16h;	83%

1-(4-(difluoromethoxy)phenyl)-2-(3-(furan-2-ylmethyl)phenyl)ethane-1,2-dione (1065169-59-6) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(2-furylmethyl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one (1065166-87-1)

Conditions	Yield
With sodium carbonate In isopropyl alcohol at 86℃; for 16h;	83%

1-(3-cyclopropyl-4-(difluoromethoxy)phenyl)-2-(3-(3-hydroxy-3-methylbut-1-ynyl)phenyl)ethane-1,2-dione (1062616-91-4) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-4-(3-cyclopropyl-4-(difluoromethoxy)phenyl)-4-(3-(3-hydroxy-3-methylbut-1-ynyl)phenyl)-1-methyl-1H-imidazol-5(4H)-one (1062608-70-1)

Conditions	Yield
With sodium carbonate In isopropyl alcohol at 86℃; for 16h;	82%

1,2-bis(3-cyclopropyl-4-(difluoromethoxy)phenyl)ethane-1,2-dione (1062617-20-2) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-4,4-bis(3-cyclopropyl-4-(difluoromethoxy)phenyl)-1-methyl-1H-imidazol-5(4H)-one (1062609-29-3)

Conditions	Yield
With sodium carbonate In isopropyl alcohol at 85℃; for 14h;	82%

1-methylguanidine hydrochloride (22661-87-6) + benzil (134-81-6) → 2-amino-3-methyl-5,5-diphenyl-3,5-dihydro-4H-imidazol-4-one (26975-80-4)

Conditions	Yield
With potassium carbonate at 90℃; for 2h; Inert atmosphere;	82%

1-methylguanidine hydrochloride (22661-87-6) → methyl guanidinium borohydride

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran at 20℃; for 18h; Inert atmosphere;	81%

1-(3-cyclopropyl-4-(difluoromethoxy)phenyl)-2-(4-fluoro-3-(3-fluoropropoxy)phenyl)ethane-1,2-dione (1062614-25-8) + 1-methylguanidine hydrochloride (22661-87-6) → 2-amino-4-(3-cyclopropyl-4-(difluoromethoxy)phenyl)-4-(4-fluoro-3-(3-fluoropropoxy)phenyl)-1-methyl-1H-imidazol-5(4h)-one (1062605-70-2)

Conditions	Yield
With sodium carbonate In ethanol at 90℃; for 3h;	80%

Upstream product

• 593-51-1 methylamine hydrochloride 
• 127099-85-8 N-Cyanoguanidine 

Downstream Products

• 344298-07-3 5-Ethoxy-2-methylamino-1H-pyrimidine-4,6-dione 
• 88075-50-7 2-amino-1-methyl-5,6-dihydro-1H-pyrimidin-4-one 
• 100185-69-1 1-(3-Ethoxypropionyl)-3-methyl-guanidin 
• 26975-77-9 N-methyl-5,5-diphenyl-2-iminohydantoin 
• 26975-80-4 3-methyl-5,5-diphenyl-2-iminohydantoin 
• 77350-26-6 2-methylamino-1H-imidazole-4,5-dione 
• 180869-38-9 4-(dimethoxymethyl)-N-methylpyrimidin-2-amine 
• 870221-22-0 4-(2-chloropyridin-3-yl)-N-methylpyrimidin-2-amine 

Relevant academic research and scientific papers

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS

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Herbicidal 3 -heterocyclic substituted benzisothiazole and benzisoxazole compounds

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SIMPLE AMIDINIUM CARBOXYLATES - AN MO TREATMENT OF MOLECULAR GEOMETRY AND ELECTRONIC STRUCTURE

Carboxylates of amidines (I,II), substituted guanidine (III) and iso(thio)ureas (IV,V) were prepared.Nonempirical quantum chemical treatment of the electronic structure of simple compounds I-V, based on total molecular geometry optimization, their preparation and physicochemical data are reported.Interaction between the two amidinium nitrogens and carboxylate oxygens is mediated by hydrogen bonds and alternation of charge distribution.