mono-Moxonidine oxalate
A
4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
B
4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
C
moxonidine
Conditions | Yield |
---|---|
With sodium hydroxide In water at 20℃; for 1h; pH=10 - 11; Product distribution / selectivity; | A n/a B n/a C 94% |
methanol
4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
A
4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
B
moxonidine
Conditions | Yield |
---|---|
With potassium carbonate at 65℃; for 3h; Product distribution / selectivity; | A n/a B 90.7% |
methanol
4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
A
4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
B
4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
C
moxonidine
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water at 65℃; for 6h; Product distribution / selectivity; | A n/a B n/a C 88.3% |
With potassium hydrogencarbonate In water at 65℃; for 10h; Product distribution / selectivity; | A n/a B n/a C 88.3% |
With potassium hydroxide; potassium carbonate at 20℃; for 16h; Product distribution / selectivity; | A n/a B n/a C 85.9% |
methanol
4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
A
4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
B
moxonidine
Conditions | Yield |
---|---|
With sodium hydroxide In water at 25℃; for 24h; Product distribution / selectivity; | A n/a B 88.3% |
With potassium hydroxide at 25℃; for 12h; Product distribution / selectivity; | A n/a B 88.3% |
4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
sodium methylate
A
4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
B
4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
C
moxonidine
Conditions | Yield |
---|---|
In methanol at 0 - 65℃; for 1.5 - 48h; Product distribution / selectivity; | A n/a B n/a C 84.7% |
In tetrahydrofuran at 25℃; for 30h; Product distribution / selectivity; | A n/a B n/a C 76.4% |
In toluene at 25℃; for 30h; Product distribution / selectivity; | A n/a B n/a C 66.8% |
methanol
4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
moxonidine
Conditions | Yield |
---|---|
With pyrographite; 1,8-diazabicyclo[5.4.0]undec-7-ene at 65℃; for 3.5h; | 84.4% |
With potassium hydroxide at 20℃; for 30h; Product distribution / selectivity; | 83.5% |
With tetrabutylammomium bromide; water; sodium hydroxide In dichloromethane at 20 - 35℃; for 2.5h; pH-value; Reagent/catalyst; Solvent; Temperature; | 3.43 g |
4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
moxonidine
Conditions | Yield |
---|---|
With potassium hydroxide In methanol; water at 20℃; for 31h; | 83.5% |
With sodium methylate In methanol; water | |
In tetrahydrofuran; methanol |
4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
sodium methylate
A
4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
B
moxonidine
Conditions | Yield |
---|---|
In methanol at 0℃; for 48h; Product distribution / selectivity; | A n/a B 77.6% |
4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
sodium methylate
A
4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
B
moxonidine
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 25℃; for 30h; Product distribution / selectivity; | A n/a B 76.4% |
4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
A
4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
B
4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
C
moxonidine
Conditions | Yield |
---|---|
Stage #1: 4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine With potassium carbonate In methanol at 47 - 52℃; for 5h; Stage #2: With water; acetic acid In methanol for 0.5h; Stage #3: With ammonia In methanol; water for 1h; Product distribution / selectivity; |
methanol
4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
1-[1-((4,6-dichloro-2-methyl-pyrimidin-5-yl)imino)-ethyl]-imidazolidin-2-one
sodium methylate
A
1-[1-[(4-chloro-2-methyl-6-methoxy-pyrimidin-5-yl)imino]ethyl]-imidazolidin-2-one
B
moxonidine
Conditions | Yield |
---|---|
at 20℃; | A 0.12 %Chromat. B 96.66 %Chromat. |
methanol
4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
sodium methylate
A
4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
B
4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
C
moxonidine
Conditions | Yield |
---|---|
for 2h; Heating / reflux; | A 1.45 - 1.48 %Chromat. B 5.27 - 5.32 %Chromat. C 93.22 - 93.25 %Chromat. |
methanol
4,6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine
sodium methylate
moxonidine
Conditions | Yield |
---|---|
at 30 - 35℃; for 0.75h; | 520 mg |
5-amino-4-methoxy-6-chloro-2-methyl-pyrimidine
moxonidine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium carbonate; trichlorophosphate / dimethyl sulfoxide / 49 h / 5 - 60 °C / Inert atmosphere 2: hydrogenchloride / isopropyl alcohol / 8 h / 20 °C 3: base / water / pH 9 View Scheme |
moxonidine
Conditions | Yield |
---|---|
With base In water pH=9; |
1-acetylimidazolidin-2-one
5-amino-4-methoxy-6-chloro-2-methyl-pyrimidine
moxonidine
Conditions | Yield |
---|---|
Stage #1: 1-acetylimidazolidin-2-one; 5-amino-4-methoxy-6-chloro-2-methyl-pyrimidine With sodium carbonate; trichlorophosphate In dimethyl sulfoxide at 5 - 60℃; for 50.5h; Cooling with acetone-dry ice; Inert atmosphere; Stage #2: With hydrogenchloride In water; isopropyl alcohol at 20℃; for 8h; |
oxalic acid
moxonidine
A
4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
B
mono-Moxonidine oxalate
Conditions | Yield |
---|---|
In methanol; diethyl ether Product distribution / selectivity; Heating / reflux; | A n/a B 95% |
In methanol; propan-1-ol at 0 - 20℃; for 3.5h; Product distribution / selectivity; Heating / reflux; | A n/a B 83.6% |
In propan-1-ol; dimethyl sulfoxide Product distribution / selectivity; Heating / reflux; | A n/a B 58% |
formic acid
moxonidine
A
4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
B
mono-Moxonidine formate
Conditions | Yield |
---|---|
In propan-1-ol at 0 - 20℃; for 4h; Product distribution / selectivity; Heating / reflux; | A n/a B 92.7% |
In isopropyl alcohol at 0 - 20℃; for 4h; Product distribution / selectivity; Heating / reflux; | A n/a B 85% |
In N,N-dimethyl-formamide at 0 - 20℃; for 4h; Product distribution / selectivity; Heating / reflux; | A n/a B 84% |
In dimethyl sulfoxide at 0 - 20℃; for 4h; Product distribution / selectivity; Heating / reflux; | A n/a B 66% |
oxalic acid
moxonidine
A
4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
B
mono-Moxonidine oxalate
Conditions | Yield |
---|---|
In propan-1-ol at 0 - 20℃; for 2h; Product distribution / selectivity; Heating / reflux; | A n/a B 87.3% |
oxalic acid
moxonidine
A
4,6-dichloro-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
B
4,6-dimethoxy-2-methyl-5-(2-imidazolin-2-yl)-aminopyrimidine
C
mono-Moxonidine oxalate
Conditions | Yield |
---|---|
In methanol; propan-1-ol at 0 - 20℃; for 3.5h; Heating / reflux; | A n/a B n/a C 87% |
moxonidine
4-methoxy-2-methyl-6-methylthio-5-(2-imidazolin-2-yl)-aminopyrimidine
Conditions | Yield |
---|---|
In toluene |
The IUPAC name of Moxonidine is 4-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxy-2-methylpyrimidin-5-amine. With the CAS registry number 75438-57-2, it is also named as 5-Pyrimidinamine, 4-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxy-2-methyl-. The product's categories are API's; Antihypertensive; Cardiovascular Agents; Drug Agent. Besides, it is crystal. In addition, its molecular formula is C9H12ClN5O and molecular weight is 241.68.
The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.41; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.39; (4)ACD/LogD (pH 7.4): -1.67; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 6; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.68; (13)Molar Refractivity: 59.81 cm3; (14)Molar Volume: 158.1 cm3; (15)Surface Tension: 51.7 dyne/cm; (16)Density: 1.52 g/cm3; (17)Melting Point: 217-219 °C; (18)Flash Point: 174.3 °C; (19)Enthalpy of Vaporization: 61.09 kJ/mol; (20)Boiling Point: 364.7 °C at 760 mmHg; (21)Vapour Pressure: 1.66E-05 mmHg at 25 °C.
Preparation of Moxonidine: first, please use 5-Amino-4,6-dichloro-2-methy pyrimidine to react with 1-Acetyl-2-imidazolidinone. And then use the resultant to react with Sodium methoxide. And you would obtain this chemical.
Uses of Moxonidine: this chemical is an antihypertensive drug licensed for the treatment of mild to moderate essential hypertension. Moreover, it is a selective agonist at the imidazoline receptor subtype 1 (I1). It can also promote sodium excretion to improve insulin resistance and glucose tolerance and protect against hypertensive target organ damage, such as kidney disease and cardiac hypertrophy.
People can use the following data to convert to the molecule structure.
(1)SMILES: Clc1nc(nc(OC)c1N/C2=N/CCN2)C
(2)InChI: InChI=1/C9H12ClN5O/c1-5-13-7(10)6(8(14-5)16-2)15-9-11-3-4-12-9/h3-4H2,1-2H3,(H2,11,12,15)
(3)InChIKey: WPNJAUFVNXKLIM-UHFFFAOYAJ
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
man | TDLo | oral | 780mg/kg/39W- (780mg/kg) | LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" LIVER: "JAUNDICE, CHOLESTATIC" SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Lancet. Vol. 350, Pg. 1822, 1997. |
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