Minoxidil | U10858 | Amines

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Quality Control of Minoxidil Purity: 95% SDS Specification

COA

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NMR

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Product Details of Minoxidil

CAS No. :	38304-91-5
Formula :	C₉H₁₅N₅O
M.W :	209.25
SMILES Code :	NC1=NC(N2CCCCC2)=CC(N)=[N+]1[O-]
Synonyms :	U10858; Loniten; Minoxidil, Loniten, Rogaine, U 10858
MDL No. :	MFCD00063409
InChI Key :	ZIMGGGWCDYVHOY-UHFFFAOYSA-N
Pubchem ID :	4201

Safety of Minoxidil

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of Minoxidil

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 38304-91-5 ]

[ 38304-91-5 ] Synthesis Path-Downstream 1~18

1
[ 38304-91-5 ]
[ 80142-45-6 ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1791 - 1793.

2
[ 110-89-4 ]
[ 35139-67-4 ]
[ 38304-91-5 ]

References: [1]Journal of Organic Chemistry,1995,vol. 60,p. 2436 - 2442.

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[ 108-24-7 ]
[ 38304-91-5 ]
[ 64675-18-9 ]

References: [1]Journal of Organic Chemistry,1995,vol. 60,p. 2436 - 2442.

Yield	Reaction Conditions	Operation in experiment
		Representative of the compounds of formula II are: 4,5-diaminopyrimidine; 4-amino-5-aminomethyl-2-methylpyrimidine; 6-(piperidino)-2,4-diaminopyrimidine 3-oxide; 4,6-diaminopyrimidine; 4,5,6-triaminopyrimidine; 4,5-diamino-6-hydroxy pyrimidine; 2,4,5-triamino-6-hydroxypyrimidine; 2,4,6-triaminopyrimidine; 4,5-diamino-2-methylpyrimidine; ...
		It is made using the following list of products. Hydrocortisone USP (micronized) Liquid Carbonis Menthol Minoxidil Beta Carotene Ergocalciferol Lanolin
		EXAMPLE 2 Topical minoxidil light gel 2%. 82.5 kg of minoxidil gel were prepared as described above using the following quantities in each part:

		Particularly preferred mixtures of minoxidil and an ester according to the invention include the following: Minoxidil and pyroglutamic acid n-pentyl ester Minoxidil and pyroglutamic acid n-hexyl ester Minoxidil and pyroglutamic acid n-heptyl ester Minoxidil and pyroglutamic acid n-octyl ester
		Stage 4 Preparation of 6-piperidino-2,4-diaminopyrimidine-3-oxide A solution of 1 g N-(6-piperidino-2-amino-3-oxide-4-pyrimidinyl),N'-butylurea in a mixture of 50 cm3 isopropanol and 25 cm3 10 N potash. was maintained at 80 C. until the starting compound had disappeared. The isopropanol was evaporated off under reduced pressure and the desired product crystallized out of the aqueous phase. This latter was diluted with 50 cm3 water and the product was filtered off.
		Stage 4 Preparation of 6-piperidino-2,4-diaminopyrimidine-3-oxide A solution of 90 g of the product obtained in the preceding stage in 750 cm3 butanol and 10 cm3 water was heated to 100 C. under agitation. 20 g pelletized potash was added in small portions. The temperature was maintained for 3 hours. After cooling, the solution was washed with water and the butanol eliminated by evaporation under reduced pressure. The product obtained was then agitated in 200 cm3 ethyl acetate at room temperature; in this way a majority of the impurities was extracted. 45 g of 6-piperidino-2,4-diaminopyrimidine-3oxide was obtained which was recrystallized from an acetonitrile-methanol mixture.
		Stage 5 Preparation of 6-piperidino-2,4-diaminopyrimidine-3-oxide N-(6-piperidino-4-amino-3-oxide-2-pyrimidinyl), N'-cyclohexylurea was reacted under conditions described in stage 4 of example 1. The reaction time for removal of the urea function in the 2-position is longer than that with the urea in the 4-position (example 1).
		Representative compounds of the present invention are: 2-hydrazino-4-hydroxy-6-methylpyrimidine; 4,5-diaminopyrimidine; 4-amino-5-aminomethyl-2-methylpyrimidine; 6-(piperidino)-2,4-diaminopyrimidine 3-oxide; 3-amino-6-methyl-1,2,4-triazin-5(2H)-one; 4,6-diaminopyrimidine; 4,5,6-triaminopyrimidine; 4,5-diamino-6-hydroxypyrimidine; 2,4,5-triamino-6-hydroxypyrimidine; ...
		Particularly preferred mixtures of minoxidil and an ester according to the invention include the following: Minoxidil and 1,1-dicyano-2-(3,4-dihydroxyphenyl)ethylene Minoxidil and 1,1-dicyano-2-(3-methoxy-4,5-dihydroxyphenyl) ethylene Minoxidil and 1-amido-1-cyano-2-(3,4-dihydroxyphenyl) ethylene Minoxidil and 1-thioamido-1-cyano-2-(3,4-dihydroxyphenyl) ethylene Minoxidil and 1,1-dicyano-2-hydroxy-2-(3,4,5-trihydroxyphenyl)ethylene.
		(b) 2,4-diamino-3-oxy-6-piperidylpyrimidine 20 g (0.067 mol) of 2,4-diamino-3-oxy-6-(p-tolylsulfonyloxy)-pyrimidine from the foregoing step and 140 ml of piperidine are heated at 80-90 C. for 2 hr. Piperidine is distilled off in vacuum. To the residue are added 50 ml of a 5% solution of sodium hydroxide in water and 50 ml of toluene, and the mixture is stirred at 20-25 C. for half an hour. The mixture is filtered and the precipitate is washed twice with 30 ml of water and once with 30 ml of toluene. 8.4 g (60%) of 2,4-diamino-3-oxy-6-piperidylpyrimidine are obtained. M.p. 255-260 C. (decomposes).
		14. and at least one number selected from the group consisting of ... Nicotinic acid Cyclandelate Erythritol tetra-nitrate Pentaerythritol tetra-nitrate Minoxidil and Quazodine
		b) 2,4-diamino-3-oxy-6-piperidylpyrimidine 20 g (0.067 mol) of 2,4-diamino-3-oxy-6-(p-tolylsulfonyloxy)-pyrimidine from the foregoing step and 140 ml of piperidine are heated at 80-90C for 2 h. Piperidine is distilled off in vacuum. To the residue are added 50 ml of a 5% solution of sodium hyrdoxide in water and 50 ml of toluene, and the mixture is stirred at 20-25C for half an hour. The mixture is filtered and the precipitate is washed twice with 30 ml of water and once with 30 ml of toluene. 8.4 g (60%) of 2,4-diamino-3-oxy-6-piperidylpyrimidine are obtained. M.p. 255-260C (decomposes).
		Particularly preferred mixtures of minoxidil and an ester according to the invention include the following: ... Minoxidil and 2-acetyl tri-n-butyl citrate Minoxidil and tri-n-propyl citrate Minoxidil and 2-O-ethyl tri-n-butyl citrate.
		EXAMPLE 7 Preparation of a Anhydrous, Non-Ionic Lipid-Free Composition With 2% Minoxidil 0.4 g of the minoxidil of Example 1 were added with stirring under ambient conditions into a beaker containing a mixture of 4 ml of propylene carbonate, 12 ml of ethanol, 2 ml of propylene glycol, and 2 ml of glycerin, all of Example 6, in order to yield a non-ionic lipid-free composition containing 2% of minoxidil.
		Example 11 A foamable liquid composition containing approximately 0.03% by weight bimatoprost and 5%, by weight minoxidil is prepared by dissolving the bimatoprost and minoxidil in an alcohol-containing solvent.
		Example 8 Aerosol An aerosol containing approximately 0.03% by weight bimatoprost and 5%, by weight minoxidil is prepared by dissolving the bimatoprost and minoxidil in absolute alcohol.
		EXAMPLE 10 2% Minoxidil solution Minoxidil polystryrensulfonate (M.W. 7 x 104) 7.892 g NaOH 1N0.8 ml Nipagine 0.1 g Nipasol 0.04 g Distilled H2O q.s. to 100 ml.
		EXAMPLE 11 2% Minoxidil solution Minoxidil polystyrensulfonate (M.W. 6 x 106) 7.621 g NaOH 1N 0.8 ml Nipagine 0.1 g Nipasol 0.04 g Distilled H2O q.s. to 100 ml.
		EXAMPLE 12 6% Minoxidil solution Minoxidil polystyrensulfonate (M.W. 7 x 104) 23.676 g NaOH 1N 2.0 ml Nipagine 0.1 g Nipasol 0.04 g Distilled H2O q.s. to 100 ml.
		EXAMPLE 13 6% Minoxidil solution Minoxidil polystyrensulfonate (M.W. 6 x 106) 22.863 g NaOH 1N 2.0 ml Nipagine 0.1 g Nipasol 0.04 g Distilled H2O q.s. to 100 ml.

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[ 38304-91-5 ]
2,6-diamino-4-(1-piperidinyl)-1-(sulfooxy)-pyrimidinium hydroxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	In N-methyl-acetamide; water;	Method A A mixture of 1.00 grams (0.00478 mole) of 2,4-diamino-6-(1-piperidinyl)-pyrimidine-3-oxide, 1.50 grams of pyridine-sulfur trioxide complex in 15 ml of dimethylformamide (DMF) is stirred for 2.5 hrs and then concentrated in vacuo. The residue is warmed on a steam bath and swirled with 60 ml of water for 2 min. The solid product is filtered and washed repeatedly with ether to give, after drying, 0.71 grams of 2,6-diamino-4-(1-piperidinyl)-1-(sulfooxy)-pyrimidinium hydroxide, inner salt. The yield is 51%. The sample is recrystallized from DMF and water, giving a product with a melting point of 188-189 C.

References: [1]Patent: US4287338,1981,A .

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[ 530-62-1 ]
[ 38304-91-5 ]
[ 122185-19-7 ]
[ 122185-20-0 ]

Yield	Reaction Conditions	Operation in experiment
57%	In N,N-dimethyl-formamide; at 20.0℃; for 4.0h;	To a suspension of minoxidil (MNX) (2.09 g, 10 mmol) in anhydrous DMF (30 mL), 1,1-carbonyldiimidazole (1.95 g, 12 mmol) was added portionwise. The resulting mixture was stirred at room temperature for 4h and was then poured into cold aqueous solution of 5% NaHCO3 (60 ml). The precipitation was occurred after stirring for about 1 min and the precipitate was filtered under vacuo and washed twice with cold H2O and once with Et2O. Compound 5a was obtained as a mixture of two regioisomers (5a/5b 80:20). The main isomer (5a) was isolated by column chromatography (SiO2, Hex/EtOAc 20:80) as a white solid (1.0 g, 57%), mp: 221-224 oC; 1H NMR (500 MHz, CDCl3, 25 oC): delta 7.83 (s, NH2, 2H); 5.74 (s, ArH, 1H); 3.57 (unresolved t, NCH2, 4H); 1.60 (m, CH2, 4H); 1.48 (m, CH2, 8H).

References: [1]Tetrahedron Letters,2010,vol. 51,p. 1989 - 1993.
[2]Tetrahedron Letters,2020,vol. 61.

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[ 65277-42-1 ]
[ 38304-91-5 ]