133627-47-1|N-(2-Chloro-4-methylpyridin-3-yl)-2-(cyclopropylamino)nicotinamide| Ambeed

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Quality Control of [ 133627-47-1 ] Purity: 95+% SDS Specification

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Product Details of [ 133627-47-1 ]

CAS No. :	133627-47-1
Formula :	C₁₅H₁₅ClN₄O
M.W :	302.76
SMILES Code :	CC1=C(NC(=O)C2=C(NC3CC3)N=CC=C2)C(Cl)=NC=C1
MDL No. :	MFCD15144663
InChI Key :	GURGGHUREHGAMI-UHFFFAOYSA-N
Pubchem ID :	9972204

Safety of [ 133627-47-1 ]

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

Application In Synthesis of [ 133627-47-1 ]

* 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 [ 133627-47-1 ]

[ 133627-47-1 ] Synthesis Path-Downstream 1~27

1
[ 133627-47-1 ]
[ 129618-40-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With diethylene glycol dimethyl ether; sodium hydride; at 100 - 125℃; for 2.5h;Inert atmosphere;	A 250 rnL, 3-neck flask, with an overhead stirrer, a thermocouple and an addition funnel purged with N2 was prepared, charged with NaH (7.14 g, 178.5 mmol, and 1.7 equiv) and diglyme (22.5 ml), and the suspension was heated to 105 C. The reaction mixture containing <strong>[133627-47-1]CYCLOR</strong> (from Step 1A) was slowly transferred into the NaH suspension over a period of 30 minutes, while keeping the temperature of the mixture at 100 - 110 C. The charge line was rinsed of <strong>[133627-47-1]CYCLOR</strong> with 5 ml diglyme. After the addition of <strong>[133627-47-1]CYCLOR</strong> was complete, the reaction mixture was held at 100 - 125 C for about 2 hours, then assayed for reaction completion, e.g. by HPLC or UPLC. The mixture was cooled to 0-5C. The excess sodium hydride was slowly quenched by the addition of 30 mL of water, while keeping the temperature below 50 C. After quenching was complete, 60 - 70 ml of diglyme/water was distilled off from the reaction mixture under reduced pressure at 70 - 80 C. 125 ml of water was added with stirring to ensure that all salt was dissolved. 51 ml of cyclohexane and 15 ml of ethanol were added while stirring and the pH of the mixture was adjusted to 6 - 8 by the addition of glacial acetic acid (19.5 g, 3.09 n2mol), upon which nevirapine precipitates as a solid. The suspension was cooled to 0 -10C, and stirred for about one hour, during which time additional nevirapine precipitated. The product was isolated by vacuum filtration, and washed successively with water (3x30m1) and a 20% ethanol: water (2x20m1) mixture. The product was dried at 90-110C under vacuum to a constant weight. In one preparation, the dried weight of crude nevirapine was 25.4 g (91%).Nevirapine crude (20g, 75.1 rnmol) and purified water (86 mL) were added to a 500 ml 3-neck round-bottom flask fitted with magnetic stirrer, thermocouple and addition funnel. The mixture was stirred at room temperature to dissolve the nevirapine and then the solution temperature was lowered to 0-5C using an ice/water bath. Conc. aq. HC1 (23.2 mL, 277.6 mmol) was added dropwise to the above slurry while keeping temperature below 5C. After HC1 addition was completed, the reaction mixture was stirred for about 30 minutes at 0-5C to make sure all nevirapine had dissolved. Activated carbon (0.6 g) was added and the mixture was stirred for at least another 30 minutes while keeping the temperature at 0-5C. The solution was filtered using a celite pad to capture the carbon. The celite pad was rinsed with 2x 10 mL water and the filtrate was re-filtered using a 4 jim filter to remove any insoluble material/fibers, etc., before moving to next step to precipitate the final product.The clarified filtrate was transferred to a 500 mL 3-neck flask fitted with a magnetic stirrer, thermocouple and an addition funnel. The solution was cooled to 0-5 C and about 10 ml NaOH (50% solution) was added drop-wise to achieve a pH between 4 and 7, while keeping temperature below 5 C. A white precipitate appeared when the desired pH was reached. The mixture was stirred for about 30 minutes and the precipitated product was isolated by vacuum filtration, washing the solid with 3x20m1 water. The wet cake was dried at 90 -110C under vacuum to a constant weight. In an exemplary synthesis, the isolated yield was 19.2g (96%) and the purity was 100% by HPLC.
83.39%		Example 8: a) Preparation of Nevirapine of formula (I) (diglyme as solvent)N-(2-Chloro-4-methyl-3 -pyridinyl)-2-cyclopropylamino)-3 -pyridine carboxamide of formula (VII; 1.0 kg; 3.305moles) was stirred in diglyme (10 litres) and potassium tertiary butoxide (1.48 kg; 13.188 moles) was then added to the mixture, which was then heated between 1000C and 1100C for 90 minutes. After completion of the reaction, the mixture was cooled between 5C and 100C, the pH of the mixture adjusted between 6.0 and 7.0 by the addition of acetic acid, diluted with chilled water (50 litres) and the nevirapine (I) separating out was filtered. The compound of formula (I) was dried.; b) Recrystallization of Nevirapine of formula (I). Nevirapine (obtained from example 8a) was added to ethylene chloride (24 litres) and refiuxed for 30 minutes at 600C - 700C. The mixture after optional charcoal treatment was EPO <DP n="22"/>concentrated partially and filtered at 50C-IO0C. The wet solid was dried at 100-1100C for 24 hours.Yield: 0.73 kg % Yield: 83.39% HPLC Purity: 99.92%.
79.96%		Example 9: a) Preparation of Nevirapine of formula (I) (toluene as solvent)N-(2-chloro-4-methyl-3-pyridinyl)-2-cyclopropylamino)-3-pyridine carboxamide of formula (VII; 1.0 kg) was stirred in toluene (10 litres) and potassium tertiary butoxide (1.48 kg; 13.188 moles) was then added to the mixture, which was then heated between 1000C and HO0C for 180-210 minutes. After completion of the reaction, the mixture was cooled between 5C and 1O0C the pH of the mixture adjusted between 6.0 and 7.0 by the addition of sulfuric acid and then diluted with water (5 litres) and again the pH was adjusted between pH 1-2 by addition of sulfuric acid. Nevirapine (I) separating out was filtered. The compound of formula (I) was dried.; b) Recrystallization of Nevirapine of formula (I). Nevirapine (obtained from example 9a) was added to ethylene chloride (24 litres) and refluxed for 30 minutes at 600C - 700C. The mixture after optional charcoal treatment was concentrated partially and filtered at 50C-IO0C. The wet solid was dried at 100-1100C for 24 hours.Yield: 0.70 kg % Yield: 79.96%HPLC Purity: 99.92%.

71%	With sodium hydrogen sulfate; copper(l) iodide; sulfuric acid; potassium tert-butylate; In diethylene glycol dimethyl ether; at 115℃;	Step l[00285] Activated cuprous iodine: Cuprous iodide (1Og) and sodium bisulfate (lmol/L,50ml) were placed in a round-bottom flask. Sulfuric acid (lmol/L, 10) was added and the solution was stirred for 15 minutes at ambient temperature. The solution was filtered; the filter cake was washed with water (5OmL) and tetrahydrofuran (50mLx3), and then dried under reduced pressure.; Step 5[00289] 11 -Cvclopropyl-5.11 -dihvdro-4-methyl-6H-dipyridor3 ,2.-b :2 ' .3 ' -el 1.41- diazepin-2-one (Nevirapine): A solution of 7V-(2-chloro-4-methylpyridin-3-yl)-2-(cyclopropylamino)nicotinamide (1Og, 33.11 mmol, 1.00 equiv) in l-methoxy-2- (2- methoxyethoxy)ethane (300 ml) was placed in a 500 ml 3 -necked round-bottom flask. The reaction was purged with nitrogen and maintained under an inert atmosphere of nitrogen. Potassium 2-methylpropan-2-olate (1 Ig, 98 mmol, 3.00 equiv) and activated cuprous iodide (5 g, 26 mmol) were added to the solution. The solution was allowed to react overnight while maintaining the temperature at 115 C in an oil bath. The solution was filtered, the filter cake was washed with ethyl acetate (5OmL), and the filtrate was collected and concentrated in vacuo using a rotary evaporator. The residue was purified by flash chromatography on silica gel (10% ethyl acetate in petroleum ether). The final product (6.3g, purity: 98%, yield:71%) was obtained as a yellow solid.
	With sodium hydride; In diethylene glycol dimethyl ether; o-xylene; at 135 - 140℃; for 1.16667 - 1.33333h;	Sodium hydride (9.15 g, 65 % w/w) was suspended in o-xylene (187.5 ml) at 25- 300C under nitrogen atmosphere and slowly heated to 130-1350C. N-(2-chloro-4- methyl-3-pyridyl)-2-(cyclopropylamino)-3-pyridine carboxamide (25 g) was dissolved in diglyme (50 ml) at 70-800C and added to the above suspension over a period of 10-20 min at 135-138C and stirred for 1 h at 135-1400C. Thereafter the reaction mixture was cooled to 5C and acetic acid (8.75 ml) was added slowly below 15C. Then cold DM water (100 ml) was added to the reaction mixture slowly below 15C and pH of the reaction mixture was adjusted to 6.5 using acetic acid (4.25 ml) at 5-100C. The temperature of the reaction mixture was raised to 20-250C and stirred for 1 h at 20-250C and product crystallizes out. The product obtained was filtered and washed with DM water (75 ml) and then with cyclohexane (50 ml) and suck dried the product under suction for 10 min. The wet product (27.5 g) was suspended in a mixture of methanol (750 ml) and DM water (175 ml) and heated to reflux at 700C, a clear solution formed. Carbon (2.5 g) was added and stirred for 30 min at reflux. Filtered the carbon in hot condition and washed with hot methanol (50 ml, 60-650C). Filtrate was concentrated under reduced pressure at 50-550C up to residual weight attained is approximately 225 g. Thereafter cooled the concentrated mass to 5-100C and stirred for 30 min at 5-100C. The product obtained was filtered and washed with cold DM water (25 ml, 5-100C), suck dried and dried at 65-7O0C under reduced pressure. <n="11"/>Yield - 17.5 gHPLC purity - 99.92 %Moisture content - 0.08 % w/w
	With sodium hexamethyldisilazane; In tetrahydrofuran; at 30 - 66℃;	EXAMPLE 5 Preparation of 11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (Nevirapine) Using sodium Hexamethyldisilazane A reaction flask equipped with a magnetic stirrer, temperature controller thermodouple, addition funnel and condenser with an oil bubbler for exclusion of ambient air was inerted with nitrogen and charged with 3.02 g (0.010 mol) of <strong>[133627-47-1]N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide</strong> from Example 4 and 30 ml of anhydrous THF. A 40% solution of sodium hexamethyldisilazane in THF (12.7 ml, 0.025 mol) was added dropwise maintaining the temperature of the reaction mixture at no more than 30 C. When the addition of the NaHMDS solution was completed, the reaction mixture was heated to reflux temperature (about 63-66 C.).When the reaction was completed (HPLC analysis), the mixture was cooled to ambient temperature.The reaction mixture was treated with 1.55 g (0.050 mol) of methanol and 0.45 g of water (0.025 mol).The mixture was concentrated on a rotary evaporator at 25-30 in.Hg with a 50-60 water bath temperature.The residual product weighing 4.44 g was triturated with 50 ml of water and the PH 10-12 solution was acidified to PH 3 by adding 10% HCl solution.The solid product was collected by filtration and the filter cake rinsed three times with 10 ml portions of water.The filter cake was dried in a vacuum oven at 50-60 C. to obtain nevirapine.
	With sodium hydride; In diethylene glycol dimethyl ether; mineral oil; at 80 - 130℃;	EXAMPLE 6 Preparation of 11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (Nevirapine) Using sodium Hydride A 500 ml 4NRB flask with stirrer, temperature controller thermocouple, addition funnel and condenser with an oil bubbler to exclude air was inerted with nitrogen and charged with 15.00 g of 60% sodium hydride in a mineral oil slurry and 120 ml of diglyme.The mixture was heated to 130 C. and treated dropwise with a solution of 41.7 g (0.138 mol) of <strong>[133627-47-1]N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide</strong>, from Example 4, in 70 ml of diglyme at 80 C. The reaction mixture was heated at 130 C. until hydrogen evolution ceased.The mixture was cooled to ambient temperature and water (6.75 g) was added dropwise cautiously.When hydrogen evolution ceased, an additional 100 ml of water was added.Acetic acid (20 ml) was added to reduce the PH of the mixture from 11-13 to about 7.An additional 100 ml of water was added and the reaction mixture stirred under ambient conditions for 30 minutes while the product crystallized.The solid product was collected by filtration and the filter cake rinsed with 100 ml of water followed by 50 ml of cyclohexane to remove any residual mineral oil from the mineral oil-sodium hydride slurry.The wet cake was dried in a vacuum oven at 50 C. for 18 hours to obtain 35.58 g of nevirapine.
		EXAMPLE 7Preparation of NevirapineSodium hydride (9.15 g, 65% w/w) was suspended in o-xylene (187.5 ml) at 25-30 C. under nitrogen atmosphere and slowly heated to 130-135 C. <strong>[133627-47-1]N-(2-chloro-4-methyl-3-pyridyl)-2-(cyclopropylamino)-3-pyridine carboxamide</strong> (25 g) was dissolved in diglyme (50 ml) at 70-80 C. and added to the above suspension over a period of 10-20 min at 135-138 C. and stirred for 1 h at 135-140 C. Thereafter the reaction mixture was cooled to 5 C. and acetic acid (8.75 ml) was added slowly below 15 C. Then cold DM water (100 ml) was added to the reaction mixture slowly below 15 C. and pH of the reaction mixture was adjusted to 6.5 using acetic acid (4.25 ml) at 5-10 C. The temperature of the reaction mixture was raised to 20-25 C. and stirred for 1 h at 20-25 C. and product crystallizes out. The product obtained was filtered and washed with DM water (75 ml) and then with cyclohexane (50 ml) and suck dried the product under suction for 10 min. The wet product (27.5 g) was suspended in a mixture of methanol (750 ml) and DM water (175 ml) and heated to reflux at 70 C., a clear solution formed. Carbon (2.5 g) was added and stirred for 30 min at reflux. Filtered the carbon in hot condition and washed with hot methanol (50 ml, 60-65 C.). Filtrate was concentrated under reduced pressure at 50-55 C. up to residual weight attained is approximately 225 g. Thereafter cooled the concentrated mass to 5-10 C. and stirred for 30 min at 5-10 C. The product obtained was filtered and washed with cold DM water (25 ml, 5-10 C.), suck dried and dried at 65-70 C. under reduced pressure. Yield-17.5 g HPLC purity-99.92% Moisture content-0.08% w/w

References: [1]Patent: WO2016/118586,2016,A1 .Location in patent: Page/Page column 16; 17.
[2]Patent: WO2007/10352,2007,A1 .Location in patent: Page/Page column 20-21.
[3]Patent: WO2007/10352,2007,A1 .Location in patent: Page/Page column 21.
[4]Patent: WO2008/103899,2008,A1 .Location in patent: Page/Page column 72; 74.
[5]Journal of Medicinal Chemistry,1991,vol. 34,p. 2231 - 2241.
[6]Journal of Heterocyclic Chemistry,1993,vol. 30,p. 771 - 779.
[7]Patent: WO2008/142528,2008,A2 .Location in patent: Page/Page column 9-10.
[8]Patent: US2004/2603,2004,A1 .Location in patent: Page 4.
[9]Patent: US2004/2603,2004,A1 .Location in patent: Page 4.
[10]Patent: US2010/125137,2010,A1 .Location in patent: Page/Page column 3.
[11]Green Chemistry,2017,vol. 19,p. 2986 - 2991.

2
[ 133627-47-1 ]
2-((2'-cyclopropylamino)-3'-pyridyl)-7-mrthyloxazolo<5,4-b>pyridine [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1993,vol. 30,p. 771 - 779.

3
[ 133627-46-0 ]
[ 765-30-0 ]
[ 133627-47-1 ]

Yield	Reaction Conditions	Operation in experiment
79%	With calcium oxide; In xylene; at 140℃;	lambda/-(2-Chloro-4-methyl-pyridin-3-yl)-2-cyclopropylamino-nicotinamide:; Cyclopropanamine (120 g, 2.11 mol, 10.00 equiv) and calcium oxide (24 g, 428.57 mmol, 2.00 <n="75"/>equiv) were added to a solution of 2-chloro-N-(2-chloro-4-methyl-pyridin-3-yl)nicotinamide (60 g, 213.52 mmol, 1.00 equiv) in xylene (300 ml) in a 1 L high pressure reactor. The solution was allowed to react overnight while maintaining the temperature at 140 C. The solution was filtered, the filter cake was washed with tetrahydrofuran (50mL><2), and the filtrate was concentrated in vacuo using a rotary evaporator. The residue was purified by flash chromatography on silica gel (10% ethyl acetate in petroleum ether) The product of JV-(2-chloro- 4-methyl-pyridin-3-yl)-2-cyclopropylamino-nicotinamide (51. Ig, purity: 95%, yield:79%) was obtained as a light yellow solid.
	With potassium fluoride; In o-xylene; at 25 - 140℃; for 5 - 9h;In autoclave;Product distribution / selectivity;	2-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridine carboxamide (10 g), potassium fluoride (6.17 g), cyclopropylamine (8.08 g) were suspended in o-xylene (30 ml) and heated to 130-1400C in autoclave for 5-6 h. Then the reaction mass was cooled to 25-30C, diluted with o-xylene (50 ml) and further heated the reaction mass to 70-75C. Thereafter, DM water (30iota ml), added and stirred for 10 min at 70-75C. The aqueous layer was separated at hot condition and organic layer was washed with DM water (30 ml) at 70-750C and organic layer was concentrated at 60-630C under reduced pressure. The concentrated mass was cooled to 25-300C and stirred for 15 min and further cooled to 5-100C and stirred for 30 min. Filtered the solid obtained and washed with chilled o-xylene (10 ml, 5-100C). Dried the obtained solid at 45- 500C under reduced pressure. Yield - 9.85 g HPLC purity - 99.28 %; 2-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridine carboxamide (100 g), potassium fluoride (22.62 g), cyclopropylamine (80.85 g) were suspended in o-xylene (300 ml) and heated to 130-1400C in autoclave for 5-9 h. Then the reaction mass was cooled to 25-30C, diluted with o-xylene (500 ml) and further heated the reaction mass to 70-750C. Thereafter, DM water (300 ml) added and stirred for 10 min at 70- 75C. The aqueous layer was separated at hot condition and organic layer was washed with DM water (300 ml) at 70-750C and organic layer was concentrated at 60-630C under reduced pressure up to residue weight attained is approximately 400 g. The concentrated mass was cooled to 25-300C and stirred for 15 min and further cooled to 5-100C and stirred for 30 min. Filtered the solid obtained and washed with chilled o-xylene (100 ml, 5-100C). Dried the obtained solid at 50-600C under reduced pressure. Yield - 97 g HPLC purity - 99.85 %; 2-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridine carboxamide (100 g), potassium fluoride (41.13 g), cyclopropylamine (80.85 g) were suspended in o-xylene (300 ml) and heated to 130-1400C in autoclave for 5-9 h. Then the reaction mass was cooled to 25-300C, diluted with o-xylene (500 ml) and further heated the reaction mass to 70-750C. Thereafter, DM water (300 ml) added and stirred for 10 min at 70- 75C. The aqueous layer was separated at hot condition and organic layer was washed with DM water (300 ml) at 70-750C and organic layer was concentrated at <n="8"/>60-63C under reduced pressure up to residue weight attained is approximately 400 gThe concentrated mass was cooled to 25-300C and stirred for 15 min and furthei cooled to 5-100C and stirred for 30 min. Filtered the solid obtained and washed wit. chilled o-xylene (100 ml, 5-1O0C). Dried the obtained solid at 50-600C under reducec pressure.Yield - 95 gHPLC purity - 99.76 %; 2-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridine carboxamide (50 g), potassium fluoride (30.85.g), cyclopropylamine (40.43 g) were suspended in o-xylene (150 ml) and heated to 130-140C in autoclave for 5-8 h. Then the reaction mass was cooled to 25-300C, diluted with o-xylene (250 ml) and further heated the reaction mass to 70-75C. Thereafter, DM water (150 ml) added and stirred for 10 min at 70- 75C. The aqueous layer was separated at hot condition and organic layer was washed with DM water (150 ml) at 70-750C and organic layer was concentrated at 60-630C under reduced pressure up to residual weight attained is approximately 200 g. The concentrated mass was cooled to 25-300C and stirred for 15 min and further cooled to 5-100C and stirred for 30 min. Filtered the solid obtained and washed with chilled o-xylene (50 ml, 5-100C). Dried the obtained solid at 45-500C under reduced pressure. Yield - 46.5 g Assay (By HPLC) - 99.9 %.
	With sodium phosphate; In o-xylene; at 130 - 140℃; for 6 - 8h;In S.S. bomb;Product distribution / selectivity;	2-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridine carboxamide (15 g), tri sodium phosphate dodecahydrate (20.21 g), cyclopropylamine (12.12 g) wen suspended in o-xylene (45 ml) and heated to 130-1400C for 6-8 h in S. S. Bomb wit. occational shaking. Then the reaction mass was cooled to 70-750C, diluted with o xylene (75 ml) and DM water (45 ml) and stirred for 10 min at 70-800C. The aqueou: layer was separated and washed the organic layer with DM water (45 ml) at 70-800C The organic layer was concentrated at 60-650C under reduced pressure. Th< concentrated mass was cooled to 5-100C and stirred for 30 min. Filtered the solk obtained and washed with chilled o-xylene (15 ml, 5-100C). Dried the obtained solic at 55-6O0C under reduced pressure. Yield - 14 g HPLC purity - 99 %;

	With sodium phosphate; In o-xylene; at 70 - 140℃; for 6 - 8h;In autoclave;Product distribution / selectivity;	2-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridine carboxamide (50 g), tri- sodium phosphate dodecahydrate (67.37 g), cyclopropylamine (40.43 g) were suspended in o-xylene (150 ml) and heated to 130-1400C for 6-8 h in autoclave. Then the reaction mass was cooled to 70-750C, diluted with o-xylene (250 ml) and DM water (150 ml) and stirred for 10 min at 70-800C. The aqueous layer was separated and washed the organic layer with DM water (150 ml) at 70-800C. The organic layer was concentrated at 60-650C under reduced pressure up to residual weight attained is <n="10"/>approximately 200 g. The concentrated mass was cooled to 5-1O0C and stirred for 30 min. Filtered the solid obtained and washed with chilled o-xylene (50 ml, 5-100C).Dried the obtained solid at 55-6O0C under reduced pressure.Yield - 46.5 gHPLC purity - 99.70 %
	With potassium fluoride; In o-xylene; at 70 - 140℃;In autoclave;Product distribution / selectivity;	EXAMPLE 1Preparation of N-(2-chloro-4-methyl-3-pyridyl)-2-(cyclopropylamino)-3-pyridine carboxamide2-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridine carboxamide (10 g), potassium fluoride (6.17 g), cyclopropylamine (8.08 g) were suspended in o-xylene (30 ml) and heated to 130-140 C. in autoclave for 5-6 h. Then the reaction mass was cooled to 25-30 C., diluted with o-xylene (50 ml) and further heated the reaction mass to 70-75 C. Thereafter, DM water (30 ml), added and stirred for 10 min at 70-75 C. The aqueous layer was separated at hot condition and organic layer was washed with DM water (30 ml) at 70-75 C. and organic layer was concentrated at 60-63 C. under reduced pressure. The concentrated mass was cooled to 25-30 C. and stirred for 15 min and further cooled to 5-10 C. and stirred for 30 min. Filtered the solid obtained and washed with chilled o-xylene (10 ml, 5-10 C.). Dried the obtained solid at 45-50 C. under reduced pressure. Yield-9.85 g HPLC purity-99.28%

References: [1]Journal of Heterocyclic Chemistry,1993,vol. 30,p. 771 - 779.
[2]Journal of Medicinal Chemistry,1991,vol. 34,p. 2231 - 2241.
[3]Patent: WO2008/103899,2008,A1 .Location in patent: Page/Page column 73-74.
[4]Patent: WO2008/142528,2008,A2 .Location in patent: Page/Page column 5; 6-7; 8.
[5]Patent: WO2008/142528,2008,A2 .Location in patent: Page/Page column 7.
[6]Patent: WO2008/142528,2008,A2 .Location in patent: Page/Page column 8-9.
[7]Patent: US2010/125137,2010,A1 .Location in patent: Page/Page column 2.

4
[ 133627-47-1 ]
[ 284686-28-8 ]

References: [1]Journal of Heterocyclic Chemistry,2000,vol. 37,p. 229 - 239.

5
[ 133627-47-1 ]
[ 284686-31-3 ]

References: [1]Journal of Heterocyclic Chemistry,2000,vol. 37,p. 229 - 239.

6
[ 133627-47-1 ]
[ 284686-29-9 ]

References: [1]Journal of Heterocyclic Chemistry,2000,vol. 37,p. 229 - 239.

7
[ 133627-47-1 ]
[ 284686-30-2 ]

References: [1]Journal of Heterocyclic Chemistry,2000,vol. 37,p. 229 - 239.

8
[ 133627-47-1 ]
11-cyclopropyl-5,11-dihydro-8-hydroxy-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2000,vol. 37,p. 229 - 239.

9
[ 49609-84-9 ]
[ 133627-47-1 ]

References: [1]Journal of Heterocyclic Chemistry,1993,vol. 30,p. 771 - 779.
[2]Journal of Medicinal Chemistry,1991,vol. 34,p. 2231 - 2241.
[3]Patent: WO2008/103899,2008,A1 .

10
[ 2942-59-8 ]
[ 133627-47-1 ]

References: [1]Journal of Heterocyclic Chemistry,1993,vol. 30,p. 771 - 779.

11
[ 23056-39-5 ]
[ 133627-47-1 ]

References: [1]Journal of Heterocyclic Chemistry,1993,vol. 30,p. 771 - 779.
[2]Journal of Medicinal Chemistry,1991,vol. 34,p. 2231 - 2241.

12
[ 133627-45-9 ]
[ 133627-47-1 ]

References: [1]Journal of Heterocyclic Chemistry,1993,vol. 30,p. 771 - 779.
[2]Journal of Medicinal Chemistry,1991,vol. 34,p. 2231 - 2241.
[3]Patent: WO2008/103899,2008,A1 .

13
[ 133627-47-1 ]
[ 133627-19-7 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2231 - 2241.

14
2-(cyclopropylamino)-3-pyridinecarbonyl chloride hydrochloride [ No CAS ]
[ 133627-45-9 ]
[ 133627-47-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; In acetonitrile; at 50℃; for 20h;	EXAMPLE 4 Preparation of N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide A solution of 2-chloro-4-methyl-3-pyridinamine (5.70 g, 0.040 mol) in 10 ml of acetonitrile was charged rapidly dropwise to a mixture of the acid chloride from Example 3, ground anhydrous potassium phosphate (8.49 g, 0.04 mol) and 40 ml of acetonitrile.The reaction mixture was heated at 50 C. for 20 hours and the reaction progress monitored by HPLC analysis.When the reaction was complete, the reaction mixture was cooled to ambient temperature and treated with 50 ml of water, giving a solution having a PH of about 4.5-5.The mixture was acidified to PH 1 by addition of dilute HCl solution and stirred for 30 min at ambient temperature.The reaction mixture was filtered to remove any insoluble material and the filtrate was basified to PH 9-10 with dilute sodium hydroxide solution and stirred for 30 minutes at ambient temperature.The mixture was then acidified to PH 7-8 by addition of dilute HCl, forming a dark oily layer on top of the solution.water was added, as this had been observed during past experiments of a similar nature to hasten crystallization.The oily layer crystallized slowly on stirring overnight.The solid product was collected and dried in a vacuum oven at 50 C. to obtain 9.37 g of the title compound.

References: [1]Patent: US2004/2603,2004,A1 .Location in patent: Page 4.

15
[ 133627-45-9 ]
[ 765-30-0 ]
[ 133627-47-1 ]

Yield	Reaction Conditions	Operation in experiment
79.64%	In toluene; at 125 - 130℃; under 775.743 Torr; for 21h;	Example 7: Preparation of 2-N'-cyclopropylamino-N-(2-chloro-4-methyl-3-pyridinyl)-3- pyridine carboxamide (VII)2-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridine carboxamide (III; 1.0 kg; 3.5587 moles) was added to toluene (6.0 litres) in an autoclave. Cyclopropyl amine (0.813 kg; 14.23 moles) was added and the mixture heated between 1250C and 1300C at a pressure of 15 psi for 21 hours. After completion of the reaction, the reaction mixture was cooled between 25C and 3O0C and washed with distilled water. The aqueous layer was separated and extracted with ethyl acetate (2.0 litres). The ethyl acetate layer was separated, combined with the toluene layer and concentrated under reduced pressure.Yield: 0.857 kg. % Yield: 79.64%.HPLC Purity: 98.14%.

References: [1]Patent: WO2007/10352,2007,A1 .Location in patent: Page/Page column 20.

16
[ 639807-18-4 ]
[ 133627-45-9 ]
[ 133627-47-1 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 8 A One-Pot Synthesis of N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide from 2-chloro-4-methyl-3-pyridinamine and 2-(cyclopropylamino)-3-pyridine Carboxylic Acid (Zwitterion) A 250 ml 4NRB flask equipped with a mechanical stirrer, condenser, addition funnel, and temperature controller thermocouple, was charged with 2-(cyclopropylamino)-3-pyridine carboxylic acid (18.46 g, 0.10 mol).thionyl chloride (22 ml, 0.30 mol) was added in a thin stream to the reaction flask with stirring and the mixture heated to reflux for 32 minutes.The reaction mixture was cooled and the condenser was replaced with a vacuum distillation head.The thionyl chloride was distilled off at 40 C. at 23 in Hg vacuum until the distillation pot contents became thick.toluene (30 ml) was added and distillation continued until about most of the liquid was distilled off.Another 30 ml of toluene was added and about one-half of the solvent was distilled off under vacuum.acetonitrile (60 ml) was added to the residual mixture.A solution of 2-chloro-4-methyl-3-pyridinamine (11.4 g, 0.080 mol) in 40 ml of acetonitrile was added dropwise and the reaction mixture heated to 50 C. and stirred overnight.Finely crushed potassium phosphate was added after the 2-chloro-4-methyl-3-pyridinamine addition.After 16 hrs at 50 C. 100 ml of water was added to the stirred reaction mixture (PH 4-5).The reaction mixture was filtered to remove a small quantity of insoluble material.The filtrate (2 layers) was basified to PH 10-11 with 50% aqueous NaOH solution and then acidified back to PH 8.Most of the product was found in the toluene layer by HPLC analysis.The toluene layer was extracted with 300 ml dilute HCl solution (PH 1).The aqueous acid layer was basified to PH 8 using 10% aqueous NaOH resulting in the separation of an oily layer that crystallized slowly with trituration.After standing over 2 days, the solid product was collected and dried in vacuuo at 50 C. to yield 21.40 g tan solid title compound.

References: [1]Patent: US2004/2603,2004,A1 .Location in patent: Page 5.

17
[ 65169-38-2 ]
[ 133627-47-1 ]

References: [1]Patent: WO2016/118586,2016,A1 .
[2]Green Chemistry,2017,vol. 19,p. 2986 - 2991.

18
[ 152362-01-1 ]
[ 133627-47-1 ]

References: [1]Patent: WO2016/118586,2016,A1 .
[2]Green Chemistry,2017,vol. 19,p. 2986 - 2991.

19
[ 6602-54-6 ]
[ 133627-47-1 ]

References: [1]Patent: WO2016/118586,2016,A1 .
[2]Green Chemistry,2017,vol. 19,p. 2986 - 2991.

20
[ 639807-18-4 ]
[ 133627-47-1 ]

References: [1]Patent: WO2016/118586,2016,A1 .
[2]Green Chemistry,2017,vol. 19,p. 2986 - 2991.

21
[ 52583-90-1 ]
[ 133627-47-1 ]

References: [1]Patent: WO2016/118586,2016,A1 .
[2]Green Chemistry,2017,vol. 19,p. 2986 - 2991.

22
[ 71493-72-6 ]
[ 133627-47-1 ]

References: [1]Patent: WO2016/118586,2016,A1 .
[2]Green Chemistry,2017,vol. 19,p. 2986 - 2991.

23
[ 111-96-6 ]
methyl 2-(cyclopropylamino)nicotinate [ No CAS ]
[ 133627-45-9 ]
[ 133627-47-1 ]

Yield	Reaction Conditions	Operation in experiment
		A 500 ml 3-neck round-bottom flask was fitted with an overhead stirrer, a thermocouple and an addition funnel under N2 The flask was charged with CAPIC (15 g, 105 mrnole, 1.0 equiv) and NaH (7.56g, 189 mmole, 1.8 equiv), followed by diglyme (75 ml, Sml/g of CAPIC). The mixture was stirred while heating to 30 C, then held at 30 - 35 C for 30 minutes, upon which gradual evolution of H2 gas was observed. The temperature of the mixture was increased to 60 C over a time period of about 3 hours. The reaction was held constant until the evolution of H2 gas had subsided, e.g. 20-30 minutes. A separate 150 mL, 3 necked flask, purged with N2, was charged with Me-CAN (21 .19 g, 192.2 mmol, 1 .05 equiv) and diglyrne (22.5 ml, lrnl/g) and the mixture was heated to -55C. The solution of Me-CAN was slowly transferred to the suspension of CAPIC anion while maintaining the temperature of the CAPIC mixture at 60 - 65 C. The charge line was rinsed of Me-CAN with 5 ml of diglyme. The resulting reaction mixture was held at 60-65 C for about 2 hours, and then assayed for reaction completion e.g. by HPLC or UPLC. After the reaction was complete, the reaction mixture was heated to 80 C and held at this temperature until used in the next step

References: [1]Patent: WO2016/118586,2016,A1 .Location in patent: Page/Page column 16; 17.

24
[ 13166-10-4 ]
[ 133627-47-1 ]

References: [1]Patent: WO2016/118586,2016,A1 .
[2]Green Chemistry,2017,vol. 19,p. 2986 - 2991.

25
methyl 2-(cyclopropylamino)nicotinate [ No CAS ]
[ 133627-45-9 ]
[ 133627-47-1 ]

References: [1]Green Chemistry,2017,vol. 19,p. 2986 - 2991.

26
[ 3430-27-1 ]
[ 133627-47-1 ]

References: [1]Patent: WO2008/103899,2008,A1 .

27
[ 133627-47-1 ]
[ 1051418-86-0 ]

References: [1]Patent: WO2008/103899,2008,A1 .

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Specialized Acylation Reagents-Vilsmeier Reagent • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Ugi Reaction

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CAS No.: 133627-47-1

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CAS No.: 133627-47-1

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[ 133627-47-1 ] Synthesis Path-Downstream 1~27

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