108290-86-4|Ethyl 2-amino-1H-pyrrole-3-carboxylate| Ambeed

CAS No. :	108290-86-4
Formula :	C₇H₁₀N₂O₂
M.W :	154.17
SMILES Code :	O=C(C1=C(N)NC=C1)OCC
MDL No. :	MFCD09953569
InChI Key :	XKJUSNOUOLSNJN-UHFFFAOYSA-N
Pubchem ID :	12111022

Safety of [ 108290-86-4 ]

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

Application In Synthesis of [ 108290-86-4 ]

* 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 [ 108290-86-4 ]

[ 108290-86-4 ] Synthesis Path-Downstream 1~55

1
[ 3587-60-8 ]
[ 108290-86-4 ]
[ 108290-88-6 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 1555 - 1560.

2
[ 108290-86-4 ]
[ 77-78-1 ]
[ 108290-89-7 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 1555 - 1560.

3
[ 107-20-0 ]
[ 50551-10-5 ]
[ 108290-86-4 ]

Yield	Reaction Conditions	Operation in experiment
47%	In ethyl acetate; for 0.333333h;Inert atmosphere; Reflux;	a. Preparation of ethyl 2-amino-lH-pyrrole-3-carboxylate. To a solution of carbethoxyacetamidine (390 mg, 3.0 mmol) in dried ethyl acetate (20 mL) under an argon atmosphere was rapidly added anhydrous chloroacetaldehyde under vigorous stirring at 22C. The reaction was stirred for 10 min and heated at reflux for 20 min. The mixture was cooled to room temperature and filtered through silica gel (15 g). The residue in the reaction flask was extracted with ethyl acetate (20 mL x 5), and filtered. The filtrate was collected and evaporated under reduced pressure to give 120 mg (47%) as a light yellow solid. [0090] 1H NMR: (500 MHz, CDC13) 5(ppm): 7.92 (br, 1H), 6.28 (t, J = 2.8 Hz, 1H), 6.15 (dd, J = 2.0 Hz, 1H), 4.94 (br, 2H), 4.24 (q, J = 7.1 Hz, 2H), 1.33 (t, J = 7.1 Hz, 3H). 13C NMR: (125 MHz, CDC13) 5(ppm): 166.5, 145.4, 110.3, 107.5, 94.5, 59.3, 14.7.
39%	With triethylamine; In ethyl acetate; at 80℃; for 2h;	[00204] A solution of ethyl 3-amino-3-iminopropanoate (500 g, 3.0 mmol) and triethyl amine (0.5 mL, 3.60 mmol) in ethyl acetate (20 mL) was charged with anhydrous 2- chloroacetaldehyde (0.32 mL, 1.65 mmol) at room temperature. The resulting solution was heated to 80C for 2h. The reaction mixture was cooled to room temperature and filtered. The solid residue obtained was suspended in ethyl acetate (2 X 20 mL) and filtered. The combined filtrate was concentrated in vacuo to afford the title compound 1 as a viscous oil (100 mg, 39%). NMR (400 MHz, CDC13) delta 8.21 (br s, 1H), 6.25 (d, J=7.5 Hz, 1H), 6.18 (d, J=7.5 Hz, 1H), 5.04 (br s, 2H), 4.35 (q, J=7.1 Hz, 2H), 1.25 (t, J=7.1 Hz, 3H).
31%	With ethyl acetate; In water; at 20 - 65℃; for 0.533333h;	Carbamimidoyl-acetic acid ethyl ester (3.357 g, 25.8 mmol) was dissolved in AcOEt (20 mL). Chloroacetaldehyde (50% solution in water, 1.8 mL, 28.7 mmol) was added rapidly at room temperature. The solution stirred for 2 minutes until a precipitant formed. The solution was then brought to 65 C. for 0.5 h. The reaction mixture was then cooled and flash chromatographed with AcOEt. Product containing fractions were concentrated to give the desired material as a green solid. 0.68 g obtained, 31% yield. 1H NMR (400 MHz, CDCl3) delta 1.32 (t, J=7.2 Hz, 3H), 4.24 (q, J=7.0 Hz, 2H), 5.08 (brs, 2H), 6.10-6.13 (m, 1H), 6.25 (t, J=3.12, 1 Hz), 8.60 (brs, 1H); MS Calcd.: 154. Found 155 (M+H).

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; chloroform; at 50 - 60℃;

15g (0.12mol, 1eq) of ethyl 3-amino-3-iminopropionate and 225 mL of tetrahydrofuran were added to the bottle, stirred and dissolved to obtain a solution of ethyl 3-amino-3-iminopropionate , placed in the beater system A.Add 114 g (0.75 mol, 6.5 eq) of 1,8-diazabicycloundec-7-ene (DBU) and 75 mL of THF to the beating bottle, stir well to obtain an alkaline solution, and place it in the beating system B in.The 200 g (0.13 mol, 1.1 eq) chloroacetaldehyde chloroform solution obtained in the previous step was added to a beating bottle and placed in the beating system C.Fill 180 mL white steel coils with THF, place the coils in a 60oC hot bath, and control the temperature between 50~60C.The respective beating speeds of the beating system A, the beating system B, and the beating system C are 2.30 g / min, 1.93 g / min, 2.14 g / min, and the three strands of materials converge at the tee.Then enter the coil for reaction with a retention time of 30 min.The receiving system concentrated the received product system containing 2-aminopyrrole-3-carboxylic acid ethyl ester to 40% at 40 C to obtain a viscous oily substance, namely 2-aminopyrrole-3-carboxylic acid ethyl ester. . The two-step yield was 48%.

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 1555 - 1560.
[2]Patent: WO2017/4408,2017,A1 .Location in patent: Paragraph 0087; 0089; 0090.
[3]Patent: WO2016/73891,2016,A1 .Location in patent: Paragraph 00204.
[4]Patent: US9447100,2016,B2 .Location in patent: Page/Page column 556; 557.
[5]Patent: CN110627701,2019,A .Location in patent: Paragraph 0039; 0042-0048; 0051-0057; 0060-0066; 0069-0075.

4
[ 108290-86-4 ]
[ 108290-92-2 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 1555 - 1560.

5
[ 108290-86-4 ]
[ 108290-91-1 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 1555 - 1560.

6
[ 108290-86-4 ]
[ 108290-95-5 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 1555 - 1560.

7
[ 108290-86-4 ]
[ 108291-04-9 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 1555 - 1560.

8
[ 108290-86-4 ]
[ 108290-97-7 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 1555 - 1560.

9
[ 108290-86-4 ]
[ 108290-99-9 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 1555 - 1560.

10
[ 108290-86-4 ]
[ 108290-94-4 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 1555 - 1560.

11
[ 108-48-5 ]
[ 13159-26-7 ]
[ 108290-86-4 ]
[ 187724-73-8 ]

Yield	Reaction Conditions	Operation in experiment
	In isopropyl alcohol;	Step 1.1: 2-(5-Amino-4-ethoxycarbonyl-1H-pyrrol-2-yl)-N-benzyl-pyridinium bromide Under an argon atmosphere, 658 mg (2.0 mmol) of N-benzyl-2-bromo-pyridinium bromide (for preparation see: J. Heterocyclic Chem. 28, 1083 (1991)) are introduced into 20 ml of abs. methylene chloride, and 308 mg (2.0 mmol) of <strong>[108290-86-4]2-amino-pyrrole-3-carboxylic acid ethyl ester</strong> [for preparation see: J. Heterocyclic Chem. 23, 1555 (1986)] are added thereto. The reaction mixture is stirred for 2 days with the exclusion of light. Since the reaction is not complete, 232 mul (2 mmol) of 2,6-lutidine and a further 0.20 mmol of <strong>[108290-86-4]2-amino-pyrrole-3-carboxylic acid ethyl ester</strong> are added. After a further 12 hours' stirring, the reaction mixture is concentrated by evaporation and the residue is digested in isopropanol. Filtering, washing with hexane and drying yield the title compound which, according to its 1 H-NMR spectrum, still contains approximately 10% N-benzyl-2-bromo-pyridinium bromide; 1 H-NMR (300 MHz, DMSO-d6): 11.45 (1H), 8.70 (d, J=7, 1H), 8.38 (t, J=7, 1H), 8.00 (d, J=7, 1H), 7.67 (t, J=7, 1H), 7.42 (m, 3H), 7.14 (d, J=7, 2H), 6.85 (d, J=3, 1H), 6.45 (sb, 2H), 5.91 (s, 2H), 4.13 (q, J=7, 2H), 1.19 (t, J=7, 3H); FAB-MS: (M+H)+ =322.

References: [1]Patent: US6140332,2000,A .

12
[ 108290-86-4 ]
2,4-dimethyl-N-(6-(thiophen-2-yl)pyridin-3-yl)pyrrolo[1,2-a]pyrimidine-8-carboxamide [ No CAS ]