1267610-26-3|1-(4-Aminophenyl)-3-morpholino-5,6-dihydropyridin-2(1H)-one| Ambeed

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Quality Control of [ 1267610-26-3 ] Purity: 95% SDS Specification

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Product Details of [ 1267610-26-3 ]

CAS No. :	1267610-26-3
Formula :	C₁₅H₁₉N₃O₂
M.W :	273.33
SMILES Code :	O=C1C(N2CCOCC2)=CCCN1C3=CC=C(N)C=C3
MDL No. :	MFCD22581648
InChI Key :	YUGIGSPFTMLIMA-UHFFFAOYSA-N
Pubchem ID :	66571904

Safety of [ 1267610-26-3 ]

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

Application In Synthesis of [ 1267610-26-3 ]

* 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 [ 1267610-26-3 ]

[ 1267610-26-3 ] Synthesis Path-Downstream 1~35

1
[ 1267610-26-3 ]
[ 545445-44-1 ]

References: [1]Synthetic Communications,2013,vol. 43,p. 72 - 79.
[2]Patent: CN104650072,2016,B .

2
[ 1267610-26-3 ]
[ 503614-91-3 ]

References: [1]Synthetic Communications,2013,vol. 43,p. 72 - 79.
[2]Patent: WO2017/13079,2017,A1 .
[3]Patent: US2017/15663,2017,A1 .

3
[ 1267610-26-3 ]
apixaban [ No CAS ]

References: [1]Synthetic Communications,2013,vol. 43,p. 72 - 79.
[2]Patent: WO2017/13079,2017,A1 .
[3]Patent: US2017/15663,2017,A1 .

4
[ 1575-61-7 ]
[ 1267610-26-3 ]
5-chloropentanoic acid [4-(5-morpholin-4-yl-6-oxo-3,6-dihydro-2H-pyridin-1-yl)phenyl]amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96.08%	With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; water; at 0 - 5℃; for 1h;	A solution of 5-chlorovaleroyl chloride (CVC, 82 gm, 0.5273 mol) in MDC (100 ml) was added to the suspension of product of example-IV (125 gm, 0.4573 mol), sodium hydroxide (22 gm, 0.55 mol), TBAB (3.75 gm) in MDC (1150 ml) and Water (49 ml) at 0-5 C. over 1 hrs. The mixture was slowly brought to 25 to 30 C., 300 ml water was added to the reaction mass and stirred for 10 min. Organic layer was separated and washed with water (200 ml), dried over anhydrous sodium sulfate and distilled atmospherically at 50 C. to get a residue. The residue was purified in EtOAc to get pale yellow solid. Yield: 172 gm, 96.08%
89.5%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 10 - 25℃;Inert atmosphere;	The 1e (10.0g, 36.6mmol) was dissolved in tetrahydrofuran (200ml) was added N, N-diisopropylethylamine (7.0g, 54.3mmol), under ice-cooling, a solution of 5-chloro-valeryl chloride (and 7.37 g, 47.6 mmol) to obtain a reaction mixture, said reaction mixture at room temperature overnight. Tracking progress of the reaction by TLC, the reaction was completed, water was added to the reaction solution, separated, washed with water three times, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure 1f (12.8g, yellow solid), yield rate: 89.5%

References: [1]Patent: US2017/15663,2017,A1 .Location in patent: Paragraph 0144.
[2]Patent: CN104650072,2016,B .Location in patent: Paragraph 0122; 0125; 0141; 0142.
[3]Synthetic Communications,2013,vol. 43,p. 72 - 79.

5
[ 100-01-6 ]
[ 1267610-26-3 ]

References: [1]Synthetic Communications,2013,vol. 43,p. 72 - 79.
[2]Patent: CN104650072,2016,B .

6
[ 1575-61-7 ]
[ 1267610-26-3 ]

References: [1]Synthetic Communications,2013,vol. 43,p. 72 - 79.
[2]Patent: CN104650072,2016,B .
[3]Patent: CN103626689,2016,B .
[4]Patent: US2017/15663,2017,A1 .
[5]Patent: US2017/15663,2017,A1 .

7
[ 1039914-85-6 ]
[ 1267610-26-3 ]

References: [1]Synthetic Communications,2013,vol. 43,p. 72 - 79.
[2]Patent: CN104650072,2016,B .
[3]Patent: US2017/15663,2017,A1 .

8
[ 38560-30-4 ]
[ 1267610-26-3 ]

References: [1]Synthetic Communications,2013,vol. 43,p. 72 - 79.
[2]Patent: CN104650072,2016,B .
[3]Patent: CN103626689,2016,B .
[4]Patent: US2017/15663,2017,A1 .

9
C₁₁H₁₁ClN₂O₃ [ No CAS ]
[ 1267610-26-3 ]

References: [1]Synthetic Communications,2013,vol. 43,p. 72 - 79.

10
[ 503615-03-0 ]
[ 1267610-26-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrazine hydrate; In methanol; water; at 40 - 70℃; for 3h;Large scale;	Add 25L of water and 25L of methanol to the 500L reactor, add 2.5kg of compound (I) and 250g of Raney cobalt under stirring, raise the temperature to 40-50 C, slowly add 2.0kg of hydrazine hydrate (content 80%), keep warm 60-70 C, reaction for 3h, the reaction was completed, filtered with diatomaceous earth, concentrated solvent was removed, and MTBE was added to the filter cake.2.20 kg of a white solid were obtained with a yield of 98% and a purity of 99.8%.
95.55%	With hydrazine hydrate; In ethanol; water; at 60 - 65℃; for 0.5h;	Hydrazine hydrate 80% (60 gm, 1.19 mol) was added drop wise at around 60-65 C. to the solution containing product of example-III (50 gm, 0.16 mol), Raney nickel (1 gm, 2%) in EtOH (750 ml) and water (150 ml). After completion of addition, stirred for 30 min at same temperature and brought to room temperature. The reaction mass was filtered through celite bed, concentrated under vacuum, added EtOAc (100 ml) and filter under suction. Dried the wet cake in air oven to afford the desired product as a cream colored solid. Yield: 43 gm; 95.55%
94%	With sodium sulfide; SPGS-550-M; water; at 50 - 55℃;	3-(Morpholin-4-yl)- 1 -(4-nitrophenyl)-5 ,6-dihydropyridin-2( 1H)-one (10 g; Formula II) was added to a reaction vessel containing an aqueous solution of SPGS-550M(20 mL, 2 wt. % in water) at ambient temperature. Sodium sulphide (20 g) was added. The reaction mixture was heated to 50C to 55C and stirred for 3 hours to 4 hours. The reaction mixture was cooled to ambient temperature. The reaction mixture was filtered, washed with dc-ionized water (30 mL), and then dried in an air oven at 45C to 50C to obtain the title compound.Yield: 94%

93.2%	With sodium disulfide; water; In ethanol; at 50 - 55℃; for 3h;Large scale;	2000L reactor by adding purified water 570kg,Stirring under the addition of sodium hexahydrate 569.7kg,Heating to 50-55 C, stirring about 30 minutes to dissolve, add sulfur 76kg, stirring and stirring for 1 hour to dissolve, prepared to obtain sodium disulfide.Followed by adding ethanol 570kg,90 kg of the compound of formula II-1,50-55 C Insulation reaction 3h,The reaction was complete and extracted with 900 kg of dichloromethane.The organic layer was washed with 500 kg of saturated brine and dried over 50 kg of anhydrous sodium sulfate for 2 hours. The dichloromethane was distilled off under reduced pressure to give 75.6 kg of the 1-1 compound, the yield was 93.2%, and the HPLC purity was 100%.As shown in Figure 1, almost no impurities in the product produced, the raw material reaction is complete.
91%	With sodiumsulfide nonahydrate; In ethanol; at 60℃; for 1h;	Compound 6 (10g, 0.033mol), NaS.9H2O (32g, 0.13mol), Anhydrous ethanol 200mol added to the reaction bottle, adding reaction bottle, 60 C reaction 1h, The ethanol was evaporated and the product was worked up as a pale yellow solid (8.3g, 0.03mol) in a yield of 91%
91%	With sodiumsulfide nonahydrate; In methanol; water; at 40 - 45℃; for 2.75h;	A solution of Sodium sulfate nonahydrate (197 g, 2.5 eq) in water (350 ml_) was dosed over 45 minutes at T=40/45C into a mixture of compound of formula (XI) (100 g,1.0 eq.) and methanol (1000 mL). The mixture was stirred at T=40/45C for additional 2 hours to reach reaction completion. The mixture was then distilled at reduced pressure and Tmax=45C until 930 ml_ of solvent were removed. The resulting slurry was cooled down to T=20/25C, kept stirring for 1 hour at this temperature and then filtered washing the wet cake with water (2 x 100 mL). Upon drying at reduced pressure and T=65C for 10 hours, 82 g of the compound of formula (X) were obtained. (91 % yield, HPLC A%: compound of formula (X) 96.16%, Said compound of formula (X) thus obtained contained the following dimer impurities: - 0,66% (HPLC A/A%) dimer impurity of formula (VI), - 1 ,50% (HPLC A/A%) dimer impurity of formula (VII).
74.1%	With sodium sulfide; water; In ethanol; at 50℃;Inert atmosphere;	The 1d (18.0g, 59.3mmol) was dissolved in ethanol (180ml) was added sodium sulfide nonahydrate (28.4g, 118.6mmol), was added water (60ml) to give a reaction mixture, and the mixture was reacted at 50 C .The reaction was refluxed overnight. Tracking progress of the reaction by TLC, the reaction was completed, the ethanol under reduced pressure, extracted three times with ethyl acetate, the combined organic phases concentrated to remove, dried over anhydrous magnesium sulfate, filtered, and the solvent removed by distillation under reduced pressure to give 1e (12.0g, yellow solid) yield: 74.1%

References: [1]Patent: CN108503580,2018,A .Location in patent: Paragraph 0042-0051.
[2]Patent: US2017/15663,2017,A1 .Location in patent: Paragraph 0143.
[3]Patent: WO2018/158620,2018,A1 .Location in patent: Page/Page column 27; 28; 29.
[4]Patent: CN103709095,2016,B .Location in patent: Paragraph 0026; 0027.
[5]Patent: CN103626689,2016,B .Location in patent: Paragraph 0033; 0049-0051.
[6]Patent: WO2017/13079,2017,A1 .Location in patent: Paragraph 00186.
[7]Synthetic Communications,2013,vol. 43,p. 72 - 79.
[8]Patent: CN104650072,2016,B .Location in patent: Paragraph 0122; 0125;0138; 0139.

11
[ 1267610-26-3 ]
C₂₇H₂₈N₄O₄ [ No CAS ]