227963-57-7|(E)-Ethyl 3-(6-aminopyridin-3-yl)acrylate| Ambeed

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Quality Control of [ 227963-57-7 ] Purity: 98% SDS Specification

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Product Details of [ 227963-57-7 ]

CAS No. :	227963-57-7
Formula :	C₁₀H₁₂N₂O₂
M.W :	192.21
SMILES Code :	O=C(OCC)/C=C/C1=CC=C(N)N=C1
MDL No. :	MFCD08061350
InChI Key :	GXLHWGSBMOMMOD-GQCTYLIASA-N
Pubchem ID :	17750163

Safety of [ 227963-57-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 227963-57-7 ]

* 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 [ 227963-57-7 ]

[ 227963-57-7 ] Synthesis Path-Downstream 1~33

1
[ 227963-57-7 ]
[ 666721-07-9 ]

Yield	Reaction Conditions	Operation in experiment
		(c) By proceeding in a manner similar to Reference Example 4(a) above but using 3-(6-amino-pyrid-3-yl)propenoic acid ethyl ester [Reference Example 5(c)] there was prepared 3-(6-amino-pyrid-3-yl)propanoic acid ethyl ester.

References: [1]Patent: US6479519,2002,B1 .

2
[ 69879-22-7 ]
[ 227963-57-7 ]

Yield	Reaction Conditions	Operation in experiment
		(c) By proceeding in a manner similar to Reference Example 5(a) above but using 6-amino-3-pyridinecarbaldehyde (prepared in a similar manner to that described in Dolk. Akad. Nauk. SSSR. 1949, 65, 843) there was prepared 3-(6-amino-pyrid-3-yl)propenoic acid ethyl ester.

References: [1]Patent: US6479519,2002,B1 .

3
[ 1072-97-5 ]
[ 140-88-5 ]
[ 227963-57-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With dichlorobis(tri-O-tolylphosphine)palladium; triethylamine; In N,N-dimethyl-formamide; at 100℃; for 6h;	To a solution of 5-bromopyridin-2-amine (0.568 g) in dimethylformamide (6 mL) were added ethyl acrylate (0.429 mL), triethylamine (0.682 mL), and dichloro di(tri(o-tolylphosphine))palladium (0.262 g). The mixture was stirred at 100 C. for 6 hours, and then thereto was added aqueous saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered, and then the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (0.520 g) (yield 82%). (0387) LC/MS, Condition D, Retention time 0.59 min, obs MS[M+1]193.1
81%	With palladium diacetate; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 100℃;Inert atmosphere; Sealed tube;	Step 1. (E)-ethyl 3-(6-aminopyridin-3-yl)acrylate To a glass bomb were charged with 5-bromopyridin-2-amine (10.0 g, 57.8 mmol), ethyl acrylate (8.14 mL, 75 mmol) and DIEA (25.2 mL, 144 mmol) in DMF (40 mL). The mixture was purged with argon, followed by addition of Pd(OAc)2 (0.649 g, 2.89 mmol) and (o-Tol)3P (3.87 g, 12.72 mmol), and finally purged thoroughly with argon. The mixture was sealed, and heated with 100 C. oil bath overnight. The reaction mixture was cooled down to room temperature, and the precipitates were removed by filtering through a thin layer of Celite. The filtrate was concentrated as much as possible via rotavap, and the residue was partitioned between EtOAc/water (150 mL/100 mL). EtOAc layer was washed with water (2*100 mL), dried over Na2SO4, and concentrated. A brown slid was obtained as crude product. The crude product was triturated with EtOAc (40 mL) and the yellow solid was collected via filtration. The filter cake was rinsed with small amount of EtOAc and dried under vacuum as the first crop of product (5.0 g). The mother liquor from trituration was stripped by dilute aqueous 1 N HCl (30 mL) and water (70 mL). Aqueous layer was transferred to a clean separate funnel, basicified with 20 mL sat. Na2CO3, and extracted with EtOAc (60 mL). EtOAc layer was dried over Na2SO4, concentrated and provided the second portion of product (4.0 g). The two crops of product were combined to afford 81% yield. LCMS (m/z) 193.2 (MH+), 0.39 min.
	With triethylamine;tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine; In dichloromethane; at 20 - 80℃;Heating / reflux;	Ethyl acrylate (0.47 mL, 4.33 mmol) was added into a stirred suspension of the amine (0.50 g, 2.89 mmol), Pd2(dba)3 (0.2646 g, 0.289 mmol), P(o-tol)3 (0.1583 g, 0.52 mmol), Et3N (0.62 mL, 4.45 mmol) and CH2CI2 (12 mL) at room temp. The reaction was heated to reflux at ~ 8O0C. When the starting material had fully depleted (monitored by LCMS), the reaction mixture was diluted with ethyl acetate (20 mL). The organic layer was then washed with NaHCO3 (2 x 10 mL) and brine (2 x 10 mL). The organic layer was dried in Na2SO4 before being filtered and concentrated in vacuo. The crude product was EPO <DP n="66"/>purifed by the Bison system and was isolated as a light yellow solid [trifluoroacetic acid (TFA) salt] (75%, 0.63 g).3-(2-Amino-pyridin-4-yl)-acrylic acid ethyl esterHPLC: 97.5 %; tR = 1.114 min; LCMS (ESI) Calcd for C10H12N2O2 [M+]: 192.0899, found 193.08 [MH]+; 1H NMR (400 MHz, CDCI3): δ 8.36 (brs, 1 H), 8.29 (s, 1 H), 8.26 (dd, J = 2.00, 9.27 Hz, 1 H), 7.56 (dd, J = 16.02 Hz, 1 H), 6.92 (d, J = 9.20 Hz, 1 H), 6.55 (d, J = 16.00 Hz, 1 H), 4.17 (q, J = 7.08 Hz, 2H), 1.24 (t, J = 7.10 Hz, 3H);13C NMR (100.5 MHz, CDCI3): 8 165.9, 155.3, 139.9, 139.5, 139.3, 119.1 , 118.1 , 117.2, 115.2, 113.1 , 60.0, 14.1.

References: [1]Patent: US10898469,2021,B2 .Location in patent: Page/Page column 43.
[2]Patent: US9242996,2016,B2 .Location in patent: Page/Page column 358; 359.
[3]Patent: WO2006/101455,2006,A1 .Location in patent: Page/Page column 64-65.

4
[ 104-53-0 ]
[ 227963-57-7 ]
[ 165459-70-1 ]
[ 910823-54-0 ]

Yield	Reaction Conditions	Operation in experiment
72%	With acetic acid; In methanol; at 20℃;	To a solution of the amine (0.48 g, 1.67 mmol) in MeOH (6.0 mL) was added (2) (0.22 mL, 1.67 mmol), (3) (0.27 g, 1.67 mmol) and AcOH (0.19 mL, 3.35 mmol) at room temperature. The reaction was stirred overnight. When LCMS had shown the full depletion of the starting material amine, 1 M HCI (15 mL) was added till pH ~ 1 before being concentrated in vacuo. NaHCO3 (20 mL) was then added and ethyl acetate (3 x 20 mL) was used to extract the aqueous layer. The combined organic extracts were then washed with brine (2 x 20 mL), before being died in Na2SO4. The mixture was then filtered and concentrated in vacuo. The crude product was purified by flash coloumn chromatography and the product was isolated as a viscous dark brown oil (72%, 0.55 g). EPO <DP n="67"/>3-r3-(Benzori,31dioxol-5-ylamino)-2-phenethyl-imidazori,2-alpyridin-6-vn-acrylic acid ethyl esterRf = 0.33 [Hexane : ethyl acetate (1 :1)]HPLC: 100 %; tR = 3.057 min; LCMS (ESI) Calcd for C27H25N3O4 [M+]: 455.1845, found 456.16 [MH]+; 1H NMR (400 MHz, CDCI3): δ 7.79 (s, 1 H), 7.54 (s, 1 H), 7.51 (d, J = 7.21 Hz1 1 H), 7.37 (d, J = 9.38 Hz, 1 H), 7.26 - 7.21 (m, 2H), 7.08 (dd, J = 1.85, 7.85 Hz, 2H), 6.57 (d, J = 8.28 Hz, 1 H), 6.35 (d, J = 15.87 HZ, 1 H), 5.89 (d, J = 2.31 Hz, 1 H), 5.85 (s, 2H), 5.74 (dd, J = 2.36, 8.29 Hz, 1H), 4.60 (brs, 1H), 4.23 (q, J = 7.12 Hz, 2H), 3.02 - 2.97 (m, 4H), 1.31 (t, J = 7.12 Hz, 3H); 13C NMR (100.5 MHz, CDCI3): δ 166.6, 148.6, 142.3, 142.2, 141.7, 141.1 , 140.7, 140.2, 128.7, 128.3, 126.0, 124.2, 121.5, 120.8, 120.1 , 118.2, 117.5, 108.7, 104.8, 100.9, 95.9, 60.6, 35.4, 29.5, 14.3.

References: [1]Patent: WO2006/101455,2006,A1 .Location in patent: Page/Page column 65-66.

5
[ 227963-57-7 ]
[ 24424-99-5 ]
[ 1246495-43-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dmap; triethylamine; In tetrahydrofuran; at 0 - 75℃; for 7h;	1.6. Ethyl (2E)-3-{6-[bis(tert-butoxycarbonyl)amino]pyridin-3-yl}acrylate 1 g (5.2 mmol) of (E)-3-(6-aminopyridin-3-yl)acrylic acid ethyl ester is dissolved in 50 ml of THF. 4.78 ml (34.34 mmol) of triethylamine and 1.65 g (13.01 mmol) of DMAP are added. The mixture is cooled to 0 C. and then 2.83 g (13.01 mmol) of Boc2O, dissolved beforehand in 5 ml of THF, are added dropwise. The mixture is brought back to AT, stirred for 1 h and then heated at 75 C. for 6 h. The mixture is evaporated and the residue is taken up with DCM; the resulting product is washed with water and dried over sodium sulphate; filtration and evaporation are carried out. The residue is purified by flash chromatography with 100 DCM/95-5 DCM-MeOH. 1.6 g are obtained (yield=80%).
77%	With dmap; triethylamine; In tetrahydrofuran; at 20℃;	To a solution of the compound of Reference example 12 (0.517 g) in tetrahydrofuran (15 mL) were added triethylamine (0.935 mL), di-tert-butyldicarbonate (1.26 g), and dimethylaminopyridine (0.035 g), and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (0.811 g) (yield 77%). (0390) LC/MS, Condition D, Retention time 1.19 min, obs MS[M+1]394.3
41%	With dmap; triethylamine; In tetrahydrofuran; at 80℃; for 8h;	Synthesis of (E)-ethyl 3 -(6-(bi s(tert-butoxycarbonyl)amino)pyridin-3 -yl)acrylate (164). <strong>[227963-57-7](E)-ethyl 3-(6-aminopyridin-3-yl)acrylate</strong> (163; 3.86 g, 20 mmol) was dissolved in THF (80 mL). Et3N (12.1 g, 120 mmol), DMAP (4.9 g, 40 mmol) and Boc2O (10.9 g, 50 mmol) were added. The reaction mixture was heated at 80 C for 8 h, concentrated under reduced pressure and purified by silica gel chromatography (5-10% EtOAc/petroleum ether) to give 3.3 g of (E)-ethyl 3-(6-(bis(tert-butoxycarbonyl)amino)pyridin-3-yl)acrylate 164 as white solid (41% yield). LCMS: m/z 393.2 [M+H], , tR=2.O8 min

With dmap; In tetrahydrofuran; at 20℃;

Step 2. (E)-ethyl 3-(6-(bis(tert-butoxycarbonyl)amino)pyridin-3-yl)acrylate To solution of <strong>[227963-57-7](E)-ethyl 3-(6-aminopyridin-3-yl)acrylate</strong> (6.6 g, 34.3 mmol) and DMAP (0.21 g, 1.7 mmol) in THF (150 mL) was added di-tert-butyl dicarbonate (15.7 g, 71.9 mmol). The mixture was stirred overnight at room temperature. The reaction was concentrated and a brown solid was obtained as crude (E)-ethyl 3-(6-(bis(tert-butoxycarbonyl)amino)pyridin-3-yl)acrylate (12.5 g, 93%). LCMS (m/z) 237.4 (MH+) 0.98 min.

References: [1]Patent: US2012/53209,2012,A1 .Location in patent: Page/Page column 9.
[2]Patent: US10898469,2021,B2 .Location in patent: Page/Page column 43-44.
[3]Patent: WO2017/31213,2017,A1 .Location in patent: Paragraph 00476; 00480.
[4]Patent: US9242996,2016,B2 .Location in patent: Page/Page column 358; 359; 360.

6
[ 227963-57-7 ]
[ 666721-11-5 ]

References: [1]Patent: US2012/53209,2012,A1 .
[2]Patent: WO2017/31213,2017,A1 .

7
[ 227963-57-7 ]
[ 1246495-44-2 ]

References: [1]Patent: US2012/53209,2012,A1 .

8
[ 227963-57-7 ]
[ 1246495-45-3 ]

References: [1]Patent: US2012/53209,2012,A1 .

9
[ 227963-57-7 ]
(E)-(4’-(2’-(2-(6-aminopyridin-3-yl)vinyl)-5,5’-bioxazol-2-yl)-3'-(trifluoromethyl)biphenyl-4-yl)(3,3-difluoroazetidin-1-yl)methanone [ No CAS ]

References: [1]Patent: WO2017/31213,2017,A1 .

10
[ 227963-57-7 ]
(E)-5-(2-(2’-(4-bromo-2-(trifluoromethyl)phenyl)-5,5’-bioxazol-2-yl)vinyl)pyridin-2-amine [ No CAS ]

References: [1]Patent: WO2017/31213,2017,A1 .

11
[ 227963-57-7 ]
(E)-3-(6-(bis(tert-butoxycarbonyl)amino)pyridin-3-yl)acrylicamide [ No CAS ]

References: [1]Patent: WO2017/31213,2017,A1 .

12
[ 227963-57-7 ]
(1S,2S)-ethyl 2-(6-aminopyridin-3-yl)cyclopropanecarboxylate [ No CAS ]
(1R,2R)-ethyl 2-(6-aminopyridin-3-yl)cyclopropanecarboxylate [ No CAS ]