69816-37-1|2-Aminoacetamidine dihydrobromide| Ambeed

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Quality Control of [ 69816-37-1 ] Purity: 97% SDS Specification

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Product Details of [ 69816-37-1 ]

CAS No. :	69816-37-1
Formula :	C₂H₉Br₂N₃
M.W :	234.92
SMILES Code :	N=C(N)CN.[H]Br.[H]Br
MDL No. :	MFCD00671486
Boiling Point :	No data available
InChI Key :	SLCZNGZFOVAAED-UHFFFAOYSA-N
Pubchem ID :	16211382

Safety of [ 69816-37-1 ]

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

Application In Synthesis of [ 69816-37-1 ]

* 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 [ 69816-37-1 ]

[ 69816-37-1 ] Synthesis Path-Downstream 1~22

1
[ 866262-83-1 ]
[ 69816-37-1 ]
6-(6-amino-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; In methanol; for 1.5h;	A mixture of 1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-phenyl-1,2-ethanedione (300 mg), aminoacetamidine dihydrobromide (259 mg) and sodium methoxide (238 mg) in MeOH (3 ml) was stirred for 1.5 hours. Water and EtOAc were added to the reaction mixture. The organic layer was separated, and dried over MgSO4. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography eluted with a mixture of n-hexane and EtOAc. The fractions were concentrated in vacuo to obtain 6-(6-amino-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (25.6 mg) as white powder. 1H NMR (DMSO-d6, δ): 0.77 (6H, d, J=6.6 Hz), 4.91 (1H, 7-plet, J=6.6 Hz), 6.74 (2H, br), 6.98 (1H, d, J=9.6 Hz), 7.1-7.5 (5H, m), 7.76 (1H, d, J=9.6 Hz), 8.01 (1H, s) Mass (ESI): 308 (M+H)+, 330 (M+Na)+

References: [1]Patent: US2005/222159,2005,A1 .Location in patent: Page/Page column 24.

2
[ 69816-37-1 ]
[ 431-03-8 ]
[ 6294-70-8 ]

Yield	Reaction Conditions	Operation in experiment
17%	With sodium hydroxide; sodium acetate; In methanol; water;	Step 1: 2-Amino-5,6-dimethylpyrazine. Glycine amidine dihydrobromide (620 mg, 2.64 mmol) was stirred in 6 mL of MeOH at -30 C (acetonitrile/CO2 bath) in a capped flask. Butanedione (232 μL, 2.64 mmol) was stirred separately in 6 mL H2O with sodium acetate (700 mg) until homogeneous. The diketone was added to the amidine solution by pipet followed by 2.5 mL of 3.6 M NaOH. The yellow solution was allowed to warm slowly to RT and was then stirred overnight. MeOH was removed by rotovap and the aqueous solution extracted 3*30 mL with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated to a yellow solid which contained some impurities. The solid was triturated with EtOAc/Et2O and filtered to give pure compound (55 mg, 17%). 1H-NMR (400 MHz, CDCl3) δ7.76 (s, 1H), 4.25 (br s, 2H), 2.40 (s, 3H), 2.37 (s, 3H)
410 mg	With sodium acetate; sodium hydride; In methanol; water; at 0℃; for 0.5h;	An aqueous solution (40.0 mL) of 2,3-butanedione (1.55 g) and sodium acetate (4.72 g) was added to a methanol solution (40.0 mL) of 2-aminoacetamidine dihydrobromide (4.24 g) at - 30C over 10 min. Furthermore, 3.6 mol/L aqueous sodium hydroxide solution (17.0 mL) was added, and the reaction mixture was stirred at 0C for 30 min and at room temperature overnight. Methanol was evaporated under reduced pressure, water was added, and the mixture was extracted 3 times with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated, and the obtained residue was purified by silica gel column chromatography (solvent; hexane/ethyl acetate=50/50 - 0/100) to give the title compound (410 mg). MS(ESI)m/z; 124[M+H]+

References: [1]Patent: US2003/69284,2003,A1 .
[2]Patent: EP3372601,2018,A1 .Location in patent: Paragraph 0853; 0854.

3
[ 69816-37-1 ]
[ 431-67-4 ]
[ 69816-35-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; sodium acetate; In methanol; water;	A mixture of 6.6 g. of 3,3-dibromo-1,1,1-trifluoropropanone, 60 ml. of water, and 6.6 g. sodium acetate was refluxed for about 10 minutes. The solution thus obtained was cooled and added dropwise to a solution of 6 g. of aminoacetamidine dihydrobromide in 90 ml. of methanol cooled to a temperature of about -30 C., followed by the addition of a solution of 3.6 g. of sodium hydroxide pellets in 25 ml. of water. The reaction mixture was stirred and warmed gradually to about 20 C. over a period of about two hours. The reaction product mixture was concentrated in vacuo to remove the methanol, and the residue extracted with ethyl acetate. There was obtained product weighing 3.6 g. and having a melting point of about 133-136 C. after recrystallization from a mixture of benzene and hexane. The product was identified by NMR spectrum and elemental analyses as 2-amino-6-trifluoromethylpyrazine. Analyses calcd. for C5 H4 F3 N3:

References: [1]Patent: US4293552,1981,A .

4
copper-II-acetate [ No CAS ]
[ 69816-37-1 ]
[ 17082-56-3 ]
[ 82103-36-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In methanol;	EXAMPLE 12 2Amino-7-phenyl-6,7,8,9-tetrahydro-5H-pyrazino-[2,3-d]azepine by method A A mixture of 35 gm (0.1 mol) of 1-phenyl-2,3,6,7-tetrahydro-4,5-bis(trimethylsilyloxy)-azepine and 750 ml of methanol was boiled for 2 hours. Thereafter, 60 gm (0.3 mol) of copper-II-acetate were added, and the mixture was boiled for 60 minutes more. Subsequently, the reaction mixture was filtered, the filtrate was evaporated, and the residue was extracted with boiling cyclohexane. The cyclohexane extract solution was evaporated, and the residue was dissolved in 250 ml of methanol, and the solution was admixed with 500 gm of ice and 20.6 gm (0.08 mol) of <strong>[69816-37-1]2-amino-acetamidine dihydrobromide</strong>. 2 N sodium hydroxide was then added dropwise to the mixture until a constant pH of 5 was reached, and the mixture was allowed to stand overnight in the refrigerator, then concentrated by evaporation, and the residue was made alkaline and extracted with methylene chloride. The dried and concentrated extract solution was chromatographed on silicagel with ethyl acetate as the mobile phase. Yield: 1.7 gm (8.9% of theory) Melting point: 95-97 C. Calculated: C: 69.97%; H: 6.71%; N: 23.22% Found: C: 69.70%; H: 6.70%; N: 23.05%.

References: [1]Patent: US4409220,1983,A .

5
[ 314041-39-9 ]
[ 69816-37-1 ]
[ 69816-39-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In methanol; chloroform; water;	To a solution of 1.8 g. of 1-phenyl-3,3,3-trifluoro-1,2-propanedione monohydrate in 40 ml. of methanol, cooled in an ice bath, there was added, with stirring, 2 g. of aminoacetamidine dihydrobromide. Stirring was continued while 8.6 ml. of aqueous 2 N sodium hydroxide was added. The reaction mixture was then stirred at room temperature for about two hours, and then stirred and refluxed for about four hours. The reaction mixture was cooled and acidified with dilute aqueous hydrochloric acid. Water was added, and the mixture extracted with 100 ml. of ethyl acetate. The ethyl acetate extract was dried over anhydrous magnesium sulfate, the drying agent filtered off, and the filtrate concentrated in vacuo. The residue thus obtained was dissolved in chloroform, and chromatographed on a silica gel column using chloroform as the eluant. There was obtained material weighing 100 mg., and identified as 2-amino-5-phenyl-6-trifluoromethylpyrazine.

References: [1]Patent: US4293552,1981,A .

6
[ 82102-92-9 ]
[ 69816-37-1 ]
2-Amino-7-butyl-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 7 2-Amino-7-butyl-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine This compound was prepared analogous to Example 3 from 1-butyl-2,3,6,7-tetrahydro-4,5-bis(trimethylsilyloxy)-azepine and <strong>[69816-37-1]2-amino-acetamidine dihydrobromide</strong>. Yield: 11.3 gm (21.4% of theory) Melting point: 140-;42 C. Calculated: C: 65.42%; H: 9.15%; N: 25.44% Found: C: 65.23%; H: 9.13%; N: 25.56%.

References: [1]Patent: US4409220,1983,A .

7
[ 82102-94-1 ]
[ 69816-37-1 ]
[ 82103-33-1 ]

Yield	Reaction Conditions	Operation in experiment
15%		EXAMPLE 9 2-Amino-7-(butyl-2)-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine This compound was prepared analogous to Example 3 from 1-(butyl-2)-2,3,6,7-tetrahydro-4,5-bis(trimethylsilyloxy)azepine and <strong>[69816-37-1]2-amino-acetamidine dihydrobromide</strong>. Yield: 15% of theory Melting point: 113 C. Calculated: C: 65.42%; H: 9.15%; N: 25.43% Found: C: 65.85%; H: 8.99%; N: 25.64%.

References: [1]Patent: US4409220,1983,A .

8
[ 82102-95-2 ]
[ 69816-37-1 ]
2-Amino-7-tert-butyl-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]-azepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%		EXAMPLE 10 2-Amino-7-tert.butyl-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]-azepine This compound was prepared analogous to Example 3 from 1-tert.butyl-2,3,6,7-tetrahydro-4,5-bis(trimethylsilyloxy)-azepine and <strong>[69816-37-1]2-amino-acetamidine dihydrobromide</strong>. Yield: 37% of theory Melting point: 128 C. Calculated: C: 65.41%; H: 9.14%; N: 25.43% Found: C: 65.20%; H: 9.18%; N: 25.49%.

References: [1]Patent: US4409220,1983,A .

9
[ 82102-96-3 ]
[ 69816-37-1 ]
2-Amino-7-cyclohexyl-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%		EXAMPLE 11 2-Amino-7-cyclohexyl-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine This compound was prepared analogous to Example 1 from 1-cyclohexyl-2,3,6,7-tetrahydro-4,5-bis(trimethylsilyloxy)azepine and <strong>[69816-37-1]2-amino-acetamidine dihydrobromide</strong>. Yield: 35% of theory Melting point: 167 C. Calculated: C: 68.26%; H: 9.00%; N: 22.74% Found: C: 68.03%; H: 9.24%; N: 22.24%.

References: [1]Patent: US4409220,1983,A .

10
[ 63588-66-9 ]
[ 69816-37-1 ]
2-amino-7-benzyl-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; bromine; In methanol; tetrachloromethane; water; pyrographite;	EXAMPLE 3 2-Amino-7-benzyl-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine by method A 70 gm (0.193 mol) of 1-benzyl-2,3,6,7-tetrahydro-4,5-bis(trimethylsilyloxy)-azepine were dissolved in 900 ml of carbon tetrachloride, and a solution of 28.8 gm (0.18 mol) of bromine in 80 ml of carbon tetrachloridewas added dropwise thereto, while cooling and stirring. The resulting mixture was concentrated by evaporation, the residue was taken up in 400 ml of methanol, the solution was admixed with 100 gm of ice, and 41.1 gm (0.175 mol) of <strong>[69816-37-1]2-amino-acetamidine dihydrobromide</strong> were added. Thereafter, 2 N sodium hydroxide was slowly added dropwise at 0 to 5 C., and when a constant pH of 5 was reached the mixture was allowed to stand in the refrigerator for 24 hours. Thereafter, the reaction mixture was evaporated, the residue was taken up in water, the solution was filtered, and the filtrate was made alkaline with sodium hydroxide. The precipitated yellowish-brown crystal slurry was suction-filtered, and the filter cake was dried in vacuo. Yield: 9.1 gm (20.4% of theory) Melting point: 112 C. An additional 5.3 gm (11.9% of theory) of the product was obtained from the aqueous filtrate by extraction with methylene chloride and subsequent column chromatographic purification of the extract solution on silicagel with methanol/methylene chloride (3:1) as the mobile phase. Calculated: C: 70.84%; H: 7.13%; N: 22.03% Found: C: 70.55%; H: 7.05%; N: 21.98%.

References: [1]Patent: US4409220,1983,A .

11
1-(4-chloro-benzoyl)-hexahydroazepine-4-one [ No CAS ]
1-(4-chloro-benzoyl)-hexahydroazepine-4,5-dione [ No CAS ]
1-(4-chloro-benzoyl)-hexahydroazepine-3,4-dione [ No CAS ]
[ 69816-37-1 ]
2-Amino-7-(4-chloro-benzoyl)-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; selenium(IV) oxide; In 1,4-dioxane; methanol; water;	EXAMPLE 13 2-Amino-7-(4-chloro-benzoyl)-6,7,8,9-tetrahydro-5H-pyrazino[2,3-d]azepine by method A 53 mg (0.2 mol) of a mixture of 1-(4-chloro-benzoyl)-hexahydroazepine-4,5-dione and 1-(4-chloro-benzoyl)-hexahydroazepine-3,4-dione [prepared from 1-(4-chloro-benzoyl)-hexahydroazepine-4-one by selenium dioxide oxidation in dioxane/water] and 47 gm (0.2 mol) of <strong>[69816-37-1]2-amino-acetamidine dihydrobromide</strong> were dissolved in 700 ml of methanol, and 200 ml of 2 N sodium hydroxide were added dropwise to the solution at 5 C. The mixture was stirred at room temperature for one hour, then concentrated by evaporation and then, after addition of more sodium hydroxide, extracted with chloroform. The dried extract solution was concentrated by evaporation and chromatographed on silicagel with ethyl acetate/methanol (10:1) as the mobile phase. The crystals obtained thereby were digested with ethyl acetate and suction-filtered. Yield: 8.8 gm (14.5% of theory) Melting point: 190-192 C. Calculated: C: 59.50%; H: 4.99%; N: 18.51%; Cl: 11.71% Found: C: 59.93%; H: 4.70%; N: 18.41%; Cl: 12.23%.

References: [1]Patent: US4409220,1983,A .

12
[ 56961-75-2 ]
[ 69816-37-1 ]
2-[Cyano-(2,3,5-trichlorophenyl)-methyl]-amino}-acetamidine Hydrobromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; water; ethyl acetate;	11. 2-[Cyano-(2,3,5-trichlorophenyl)-methyl]-amino}-acetamidine Hydrobromide Aminoacetamidine dihydrobromide (162.1 g, 0.774 mole) was added in portions to a solution of 2,3,5-trichlorobenzaldehyde (200.0 g, 0.851 mole) in methanol (2.43 litres) at room temperature. Once the addition was complete potassium cyanide (50.4 g, 0.774 mole) was added in one portion to the resulting mixture. The suspension was then stirred at 25 C. for 4 hours before being warmed to 50 C. The mixture is stirred at 50 C. for 24 hours. Methanol was then removed in vacuo, the resulting solid was slurried in water (1.5 litres) and ethyl acetate (2.5 litres) and collected by filtration. The solid was then dried in vacuo at 50 C. overnight to give the desired product. Yield 96.31 g (33.4%), 1H nmr (d-6 DMSO) δ/ppm 8.72 (3H, br, NH); 7.99 (1H, d, J 2.3 Hz, ArH); 7.79 (1H, d, J 2.3 Hz, ArH; 5.39 (1H, d, J 10.6 Hz, ArCH(CN)NH); 4.35 (1H, m, ArCH(CN)NH); 3.56 (2H, d, J 6.4 Hz, ArCH(CN)NHCH2C(=NH)NH2).

References: [1]Patent: US6255307,2001,B1 .

13
[ 69816-37-1 ]
[ 6334-18-5 ]
2,6-diamino-3-(2,3-dichlorophenyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Potassium cyanide (500 mg, 7.7 mmol) and 2-aminoacetamidine dihydrobromide (1.77 g, 7.5 mmol) were stirred in methanol (15 ml) at room temperature for 1 hour. 2,3-Dichlorobenzaldehyde (1.34 g, 7.68 mmol) was added and the suspension was stirred at room temperature overnight. Lithium hydroxide monohydrate (1.0 g, 23.8 mmol) was added and the mixture was stirred whilst open to the atmosphere at room temperature for 24 hours. The reaction mixture was partitioned between ethyl acetate (80 ml) and water (50 ml). The ethyl acetate solution was washed with water (30 ml), then dried over anhydrous sodium sulphate and evaporated in vacuo to give a light brown gum. This was purified using silica gel column chromatography, eluting with ethyl acetate, to furnish 370 mg of the title product as a brown gum. 1HNMR (CDCl3): 4.26 (br s, 2H), 4.43 (br s, 2H), 7.26 (d, 1H), 7.31 (m, 1H), 7.46 (s, 1H), (7.50 (d, 1H) MS m/z 257 [MH]+

References: [1]Patent: US2007/105872,2007,A1 .Location in patent: Page/Page column 27-28.

14
[ 151-50-8 ]
[ 69816-37-1 ]
[ 119895-68-0 ]
[ 1174186-33-4 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; at 20 - 50℃; for 28h;	2,6-Diamino-3-(2,2-difluorobenzodioxol-4-yl)pyrazine [C E N -89]; Step i; 2-[Cyano-(2,2-difluorobenzodioxol-4-yl)methyl]amino}acetamidine hydrobromide; Aminoacetamidine dihydrobromide (1.14 g, 4.9 mmol) was added in portions to a solution of 4-formyl-2,2-difluorobenzodioxole (1.0 g, 5.4 mmol) in methanol (25 ml). Potassium cyanide (0.32 g, 4.9 mmol) was then added in a single portion and the mixture was stirred at room temperature for 4h and then at 50 0C for 24 h. The mixture was cooled and the solvent removed in vacuo. The residue was slurried in ethyl acetate (25 ml) and water (14 ml) and the tan solid removed by filtration and dried. Yield 0.40 g

References: [1]Patent: WO2009/90431,2009,A1 .Location in patent: Page/Page column 52.

15
[ 69816-37-1 ]
[ 431-67-4 ]
[ 1188929-78-3 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 22.5 g sodium acetate in 230 ml water was added 21.5 g 3,3-dibromo-1,1,1-trifluoropropanone at reflux and the mixture was refluxed for 10 min. The resulting solution was cooled to 0 C. in an acetone ice bath and added dropwise to a suspension of 19.5 g aminoacetamidine dihydrobromide in 250 ml methanol at -30 C. (dry ice acetone cooling) so that the temperature did not rise above -30 C. during the addition. To the resulting solution was added dropwise a solution of 12.285 g sodium hydroxide in 100 ml water. The mixture was then allowed to warm to room temperature (warm water bath) and then stirred at room temperature for 3 h. The dark reaction mixture was concentrated under aspirator vacuum to remove methanol and extracted with ethyl acetate (4 times). The phases were separated and the organic phase was washed with brine, treated with charcoal and dried with sodium sulfate and evaporated. To the concentrated yellow solution was added heptane and the mixture was seeded whereby crystallization was initiated. The mixture was stirred at room temperature to complete crystallization. The solid was collected by filtration to yield 8.81 g of the title compound as light yellow crystals. The aqueous layers were kept at room temperature for 72 h and then extracted (2 times) with ethyl acetate. The combined organic layers were treated with charcoal and sodium sulfate and evaporated. The residue was taken up in dichloromethane and heptane was added. The mixture was concentrated again until crystallization occurred. The solid was collected by filtration to yield another 2.06 g of the title compound as light yellow crystals. MS (M-H) at 162.1.

References: [1]Patent: US2009/247550,2009,A1 .Location in patent: Page/Page column 9.

16
[ 1240048-73-0 ]
[ 69816-37-1 ]
[ 1240048-82-1 ]

Yield	Reaction Conditions	Operation in experiment
30%	With sodium ethanolate; In ethanol; at 85℃; for 4h;	Intermediate 13: te/f-Butyl 2-(aminomethyl)-8-(1-(4-chlorophenyl)cyclobutyl)-5,6-dihydropyrido[3,4- d]pyrimidine-7(8H)-carboxylate; A solution of intermediate 6 (0.5 g; 1.2 mmol), aminoacetamidine dibromide (0.35 g; 1.2 eq) and freshly prepared sodium ethoxide (0.14 g sodium; (5 eq) in 5 ml ethanol) in etha- nol (5 ml) was stirred at 85C for 4h. The solvent was removed under reduced pressure and the residue was diluted with EtOAc and water. The layers were separated and the organic layer was washed with water, brine, dried over MgSO4 and evaporated. The resi- due was purified by silica gel column chromatography to give the product (0.153 g; 30 %) as brown oil. ESI-MS [M+H+] = 429 Calculated for Ci8H2iCIN4 = 428

References: [1]Patent: WO2010/92181,2010,A1 .Location in patent: Page/Page column 90.

17
[ 96-26-4 ]
[ 69816-37-1 ]
[ 141-46-8 ]
[ 5521-58-4 ]
2-(5-aminopyrazin-2-yl)ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In aq. phosphate buffer; at 85℃; for 24h;pH 7.4;	Pyrazine derivatives were synthesized from a one-pot reaction, in which 1,3-dihydroxyacetone, glycolaldehyde, and 2-aminoacetamidine-dihydrobromide (0.10 M 1:1:1 ratio) were mixed in aqueous solution with sodium phosphate (0.25 M) atpH 7.4 by addition of NaOH, then heated to 85 C for 24 h. In a2-mL microvial, reaction contents were de-aerated and purged with nitrogen before being sealed under vacuum. A 1.0 mL aliquot of the product mixture was diluted with 8 mL of water,and a 5 mL portion was then desalted on a 20 mL Discovery DSC-18 column (Supelco, Bellefonte, PA, USA). Material was eluted with 36 mL water and 44 mL 50% methanol/water, collected in 20 separate fractions. Salt-free fractions 10-20(from 37-80 mL eluent) were combined and concentrated to 0.5 mL syrup using a CentriVap centrifuge. After storage at -20 C, the mixture was suspended in 200 μL water, and 50 μL aliquots were further diluted in 300 μL water for adequate ampoule sampling volume.

References: [1]Journal of the American Society for Mass Spectrometry,2016,vol. 27,p. 897 - 907.

18
[ 3008-40-0 ]
[ 69816-37-1 ]
C₇H₉N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15.83%	In ethanol; at 0℃; for 0.166667h;	To a solution of compound 179.1 (0.1 OOg, O. lOmmol, l .Oeq) in ethanol (5mL) at 0C, aminoacetamide dihyrobromide (0.23g, O. lOmmol, l .Oeq) was added. Reaction mixture was stirred for 10 min. Then, pH of the reaction mixture was adjusted to 8-9 by using ammonium hydroxide solution. Reaction mixture was stirred at room temperature overnight. After completion of the reaction, pH of the reaction mixture was adjusted to 7 by using IN HC1 and extracted with dichloromethane. Organic layer was combined, dried over sodium sulfate, filtered and concentrated to obtain pure 179.2 (0.021g, 15.83%). MS(ES): m/z 136.48 [M]+

References: [1]Patent: WO2018/71794,2018,A1 .Location in patent: Paragraph 00826; 00828.

19
1,2-bis(4-chlorophenyl)-3-(dimethylamino)prop-2-en-1-one [ No CAS ]
[ 69816-37-1 ]
(4,5-bis(4-chlorophenyl)pyrimidin-2-yl)ethanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.17 g	With sodium ethanolate; In ethanol; at 80℃; for 4h;	1,2-Bis(4-chlorophenyl)-3-(dimethylamino)prop-2-en-1-one (1.3 g) synthesized in Reference Example 125 was dissolved in ethanol (20 mL). To the solution, 2-aminoacetamidine dihydrobromide (1.1 g) and sodium ethoxide (1.4 g) were then added, and the mixture was stirred at 80 C. for 4 hours. The reaction mixture was cooled to room temperature and then filtered, and the filtrate was concentrated. Diethyl ether was added to the residue, followed by extraction with 1 mol/L hydrochloric acid. The aqueous layer was neutralized with a 1 mol/L aqueous sodium hydroxide solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (aminesilica, n-hexane/ethyl acetate) to obtain the title compound (0.17 g). 1H-NMR (CDCl3) δ: 4.21 (2H, s), 7.12-7.14 (2H, m), 7.28-7.41 (6H, m), 8.67 (18H, s). MS (ESI) [M+H]+: 330.

References: [1]Patent: US2019/233376,2019,A1 .Location in patent: Paragraph 1165-1168.

20
tert-butyl N-[(1S)-3-(5-bromo-2-pyridyl)-1-methyl-2,3-dioxo-propyl]carbamate [ No CAS ]
[ 69816-37-1 ]
tert-butyl N-[(1S)-1-[6-amino-3-(5-bromo-2-pyridyl)pyrazin-2-yl]ethyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate; In isopropyl alcohol; at 20℃; for 2.5h;	To a solution of tert-butyl N-[(1 S)-3-(5-bromo-2-pyridyl)-1 -methyl-2,3-dioxo-propyl]carbamate (500 mg, 0.894 mmol) in isopropanol (13.4 ml_) was added 2-aminoacetamidine dihydrobromide (1 .21 g, 4.1 1 mmol). Potassium acetate (266 mg, 2.68 mmol) was added. The reaction mixture was stirred at room temperature for 2.5 hours in the presence of air. The reaction was quenched with water and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the crude material by reverse phase chromatography (C18, eluting with ACN in water) afforded tert-butyl N-[(1 S)-1 -[6- amino-3-(5-bromo-2-pyridyl)pyrazin-2-yl]ethyl]carbamate. LCMS: Rt 1 .00, m/z = 394-396 (M+H+) (Bromo pattern); 1H-NMR (600 MHz, CDCb) d ppm: 1 .45 (br s, 9H) 1 .47 (d, J=6.7 Hz, 3H) 4.84 (br s, 2H) 5.66 - 5.74 (m, 1 H) 5.89 (br s, 1 H) 7.86 - 7.88 (m, 1 H) 7.89 (br d, J=2.0 Hz, 1 H) 7.90 (s, 1 H) 8.72 (s, 1 H).
	With potassium acetate; In isopropyl alcohol; at 20℃; for 2.5h;	2-aminoacetamidine dihydrobromide (1.21 g, 4.11 mmol) was added to a mixture of tert-butyl N-[(1S)- 3-(5-bromo-2-pyridyl)-1-methyl-2,3-dioxo-propyl]carbamate (500 mg, 0.894 mmol) in 2-propanol (13.4 mL). Potassium acetate (266 mg, 2.68 mmol) was added, and the mixture was stirred at room temperature for 2.5 hours. Water was added, the aqueous layer was extracted with ethyl acetate, the organic layer was washed with brine, dried over magnesium sulfate and concentrated. The crude mixture was purified by reverse-phase chromatography (C18 column, gradient of acetonitrile in water) to give tert-butyl N-[(1S)-1-[6-amino-3-(5-bromo-2-pyridyl)pyrazin-2-yl]ethyl]carbamate.LCMS (method 1): Retention time 1.04 min, m/z = 394-396 [M+H+] (Bromo pattern);1H NMR (600 MHz, CDCl3) d ppm: 1.45-1.47 (m, 12H) 4.84 (br s, 2H) 5.66 - 5.74 (m, 1H) 5.89 (br s, 1H) 7.86-7.88 (m, 1H) 7.89 (br d, 1H) 7.90 (s, 1H) 8.72 (s, 1H).

References: [1]Patent: WO2020/208036,2020,A1 .Location in patent: Page/Page column 87.
[2]Patent: WO2020/201398,2020,A1 .Location in patent: Page/Page column 105.

21
2,3-diphenyloxirane [ No CAS ]
[ 69816-37-1 ]
[ 41270-71-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With lithium bromide; In 1,4-dioxane; at 5 - 20℃; for 6h;Molecular sieve; Inert atmosphere; Reflux;	Add 65mmol 2-aminoacetamidine hydrobromide, 2.5mmol lithium bromide, 7.5g molecular sieve and 100mL 1,4-dioxane into the reaction flask, stir at room temperature, fill with nitrogen, and reduce the temperature of the reaction system by 5-10C, and then Dissolve 50mmol of formula III compound in 50mL 1,4-dioxane and drop it into the above reaction flask. After dropping, stir and react at room temperature for 3h, then heat to reflux and keep the reaction at reflux for 3h, stop heating, and cool to After filtering at room temperature, the filtrate was distilled to dryness under reduced pressure, 150 mL of water was added, stirred for 0.5 h, the precipitated solid was filtered, the crude solid was recrystallized with ethanol, and dried under reduced pressure to obtain the compound of formula IV with a yield of 87%.

References: [1]Patent: CN113214169,2021,A .Location in patent: Paragraph 0026; 0054-0062.

22
2-{2-([1,1'-biphenyl]-4-yl)-4-methylthiazol-5-yl}-5-(methylsulfonyl)-1,3,4-oxadiazole [ No CAS ]
[ 69816-37-1 ]
2-[5-(2-((1,1’-biphenyl)-4-yl)-4-methylthiazol-5-yl)-1,3,4-oxadiazol-2-yl]amino}acetimidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃;Inert atmosphere;	General procedure: The methylsulfone 6 (0.1 g, 0.26mmol) was stirred in dry DMF (5 mL) to complete dissolution, and then a proper alkylamine(0.4 mmol), used as obtained for the commercial source, was added. The reaction mixtureswere flushed with dry nitrogen and heated to 80 C. The progress of the reaction was monitoredby TLC. After consuming all starting materials in a period ranging from 0.5 to 12 h, thereaction mixture was allowed to cool to room temperature and quenched with ice water (50mL). The formed solids were filtered, washed with 50% ethanol and purified by crystallizationfrom absolute ethanol to yield the desired products. The yields, physical properties and spectralanalyses of isolated products are listed below:

References: [1]PLoS ONE,2021,vol. 16.

Historical Records

Technical Information

• Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Heat of Combustion • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Similar Product of
[ 69816-37-1 ]

A479644 [27757-71-7]

2-Aminoacetimidamide

Reason: Free-salt

A425075 [27757-71-7]

2-Aminoacetimidamide

Reason: Free-salt

Related Functional Groups of
[ 69816-37-1 ]

Aliphatic Chain Hydrocarbons

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2-Aminoacetimidamide

Similarity: 0.92

Amidines

A479644 [27757-71-7]

2-Aminoacetimidamide

Similarity: 0.92

Amines

A479644 [27757-71-7]

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Similarity: 0.92

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CAS No.: 69816-37-1

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