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2-Ethylpyrazine is an endogenous metabolite.

4.5 *For Research Use Only !

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Quality Control of 2-Ethylpyrazine Purity: 98% SDS Specification

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Product Details of 2-Ethylpyrazine

CAS No. :	13925-00-3
Formula :	C₆H₈N₂
M.W :	108.14
SMILES Code :	CCC1=NC=CN=C1
MDL No. :	MFCD00006149
InChI Key :	KVFIJIWMDBAGDP-UHFFFAOYSA-N
Pubchem ID :	26331

Safety of 2-Ethylpyrazine

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H225-H302
Precautionary Statements:	P210-P233-P240-P241-P242-P301+P312
Class:	3
UN#:	1993
Packing Group:	Ⅲ

Application In Synthesis of 2-Ethylpyrazine

* 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 [ 13925-00-3 ]

[ 13925-00-3 ] Synthesis Path-Downstream 1~42

1
[ 13925-00-3 ]
[ 98-97-5 ]

References: [1]Journal of Organic Chemistry,1959,vol. 24,p. 691.
[2]Journal of Chemical Thermodynamics,2005,vol. 37,p. 49 - 53.

2
[ 13961-37-0 ]
[ 13925-00-3 ]

References: [1]Journal of Organic Chemistry,1959,vol. 24,p. 691.

3
[ 110-85-0 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 13925-00-3 ]
[ 109-97-7 ]

References: [1]Chemistry of Heterocyclic Compounds,1993,vol. 29,p. 1308 - 1315.
    Khimiya Geterotsiklicheskikh Soedinenii,1993,p. 1516 - 1525.
[2]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1990,vol. 39,p. 1340 - 1345.
    Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1990,p. 1483 - 1488.
[3]Chemistry of Heterocyclic Compounds,1993,vol. 29,p. 1308 - 1315.
    Khimiya Geterotsiklicheskikh Soedinenii,1993,p. 1516 - 1525.

4
[ 110-85-0 ]
[ 288-32-4 ]
[ 290-37-9 ]
[ 616-47-7 ]
[ 109-08-0 ]
[ 13925-00-3 ]
[ 693-98-1 ]

References: [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1990,vol. 39,p. 1340 - 1345.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1990,p. 1483 - 1488.

5
[ 13925-00-3 ]
[ 100-52-7 ]
[ 109243-30-3 ]
[ 109243-29-0 ]

References: [1]Journal of Organic Chemistry,1987,vol. 52,p. 3971 - 3974.

6
[ 13925-00-3 ]
2-(1'-bromoethyl)pyrazine [ No CAS ]

References: [1]Agricultural and Biological Chemistry,1983,vol. 47,p. 729 - 738.

7
[ 123-84-2 ]
[ 109-08-0 ]
[ 13925-00-3 ]

References: [1]Chemistry of Heterocyclic Compounds,1993,vol. 29,p. 1308 - 1315.
Khimiya Geterotsiklicheskikh Soedinenii,1993,p. 1516 - 1525.

8
[ 123-84-2 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 13925-00-3 ]
[ 693-98-1 ]
[ 15707-23-0 ]

References: [1]Chemistry of Heterocyclic Compounds,1993,vol. 29,p. 1308 - 1315.
Khimiya Geterotsiklicheskikh Soedinenii,1993,p. 1516 - 1525.

9
[ 107-15-3 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 13925-00-3 ]

References: [1]Chemistry of Heterocyclic Compounds,1993,vol. 29,p. 1308 - 1315.
Khimiya Geterotsiklicheskikh Soedinenii,1993,p. 1516 - 1525.
[2]Chemistry of Heterocyclic Compounds,1993,vol. 29,p. 1308 - 1315.
Khimiya Geterotsiklicheskikh Soedinenii,1993,p. 1516 - 1525.

10
[ 56-45-1 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 13925-00-3 ]
[ 13925-03-6 ]

References: [1]Journal of Agricultural and Food Chemistry,1999,vol. 47,p. 4332 - 4335.

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 3 With the same catalyst and reaction conditions as those of Example 1, 15.8 grams of ethylpyrazine were obtained by the feeding of 20 grams of N-(2-butylhydroxy)ethylenediamine for 1 hour. Gas chromatographic analysis gave ca. 100percent conversion and 96.4percent selectivity on ethylpyrazine.
		...ethylthiazoline, 2-isobutyl-4,5-dimethyl-3-thiazoline, 4-methylthiazole, 2-methylthiazole, 2-acetyl-2-thiazole, 2,4,5-trimethylthiazole, 2,4-dimethyl-5-ethylthiazole, 5-hydroxyethyl-4-methylthiazole, 1,3-benzothiazole, 1,3-thiazolidine, 2-methyl-1,3- thiazolidine, 2-isopropyl-1,3-thiazolidine,2-methylpyrazine, 2-ethylpyrazine, 2-propylpyrazine, 2-isopropylpyrazine, 2-methoxypyrazine, 2,3-dimethylpyrazine, 2,5-dimethylpyrazine, 2,6-dimethylpyrazine, 2,3,5-trimethylpyrazine, 2,3,5,6-tetramethylpyrazine, 2-methyl-3-ethylpyrazine 2-ethyl-3,5-dimethylpyrazine, 2-ethyl-3,6-dimethylpyrazine, 3-ethyl-2,5-dimethylpyrazine, 2,3-diethyl-5-methylpyrazine, 3-isobutyl-2-methoxypyrazine, 3-isopropyl-2-methoxypyrazine, 2-acetylpyrazine, 2-acetyl-3-methylpyrazine, 5-acetyl-2-methylpyrazine, 6-acetyl-2-ethylpyrazine,2-methylpropanal, 2-methybutanal, 3-methylbutanal, 4-pentenal, (E)-2-nonenal, hexanal, (E)-2-hexenal, 2,4-hexadienal, heptanal, 4-heptenal, octanal, (E)-2-octenal, octadienal, nonanal, (E,E)-2,4-nonadienal, (2E,6Z)-nonadienal, (E,E)-2,4-decadienal, (E,Z)-2,4-decadienal, (E)-2-undecenal, 12-methyl-tridecanal,3-methyl-1-butanol, 1-pentanol, 1-penten-3-ol, 3-cis-hexenol, 3-methyl-2-hexen-1-ol, 1-heptanol, 3-octanol, 1-octene-3-ol,3-hydroxy-2-butanone, 2-butanone, 2,3-butanedione, 2-pentanone, methyl isobutyl ketone, 1-pentene-3-one, 2-hexanone, oct-1-en-3-one, 2,3-octanedione, 2-nonanone, 2-decanone, 4-undecanone, 2-tridecanone, 3-methylcyclopentanone, 3-methylcyclopentenone, methyl cyclopentenolone, dimethyl cyclopentenolone, ethyl cyclopentenolone,gamma-hexalactone, gamma-octalactone, gamma-decalactone, gamma-dodecalactone, delta-nonalactone,butyric acid, isobutyric acid, isovaleric acid, pentanoic acid, hexanoic acid, isocaproic acid, heptanoic acid,
		...line, 2-isobutyl-4,5-dimethyl-3-thiazoline, 4-methylthiazole, 2-methylthiazole, 2-acetyl-2-thiazole, 2,4,5-trimethylthiazole, 2,4-dimethyl-5-ethylthiazole, 5-hydroxyethyl-4-methylthiazole (sulfurol), 1,3-benzothiazole, 1,3-thiazolidine, 2-methyl-1,3- thiazolidine, 2-isopropyl-1,3-thiazolidine,2-methylpyrazine, 2-ethylpyrazine, 2-propylpyrazine, 2-isopropylpyrazine, 2-methoxypyrazine, 2,3-dimethylpyrazine, 2,5-dimethylpyrazine, 2,6-dimethylpyrazine, 2,3,5-trimethylpyrazine, 2,3,5,6-tetramethylpyrazine, 2-methyl-3-ethylpyrazine 2-ethyl-3,5-dimethylpyrazine, 2-ethyl-3,6-dimethylpyrazine, 3-ethyl-2,5-dimethylpyrazine, 2,3-diethyl-5-methylpyrazine, 3-isobutyl-2-methoxypyrazine, 3-isopropyl-2-methoxypyrazine, 2-acetylpyrazine, 2-acetyl-3-methylpyrazine, 5-acetyl-2-methylpyrazine, 6-acetyl-2-ethylpyrazine,2-methylpropanal, 2-methybutanal, 3-methylbutanal, 4-pentenal, (E)-2-nonenal, hexanal, (E)-2-hexenal, 2,4-hexadienal, heptanal, 4-heptenal, octanal, (E)-2-octenal, octadienal, nonanal, (E,E)-2,4-nonadienal, (2E,6Z)-nonadienal, (E,E)-2,4-decadienal, (E,Z)-2,4-decadienal, (E)-2-undecenal, 12-methyl-tridecanal,3-methyl-1-butanol, 1-pentanol, 1-penten-3-ol, 3-cis-hexenol, 3-methyl-2-hexen-1-ol, 1-heptanol, 3-octanol, 1-octene-3-ol,3-hydroxy-2-butanone (acetoin), 2-butanone, 2,3-butanedione (diacetyl), 2-pentanone, methyl isobutyl ketone, 1-pentene-3-one, 2-hexanone, oct-1-en-3-one, 2,3-octanedione, 2-nonanone, 2-decanone, 4-undecanone, 2-tridecanone, 3-methylcyclopentanone, 3-methylcyclopentenone, methyl cyclopentenolone (3-methyl-1,2-cyclopentanedione), dimethyl cyclopentenolone (3,4-dimethyl-1,2-cyclopentanedione, 3,5-dimethyl-1,2-cyclopentanedione), ethyl cyclopentenolone (3-ethyl-1,2-cyclopentanedione),gamma-hexalactone, gamma-octalactone, gamma-decalactone, gamma-dodecalactone, delta-nonalactone,butyric acid, isobutyric acid, isovaleric acid, pentanoic acid, hexanoic acid, isocaproic acid, heptanoic acid,

...line, 2-isobutyl-4,5-dimethyl-3-thiazoline, 4-methylthiazole, 2-methylthiazole, 2-acetyl-2-thiazole, 2,4,5-trimethylthiazole, 2,4-dimethyl-5-ethylthiazole, 5-hydroxyethyl-4-methylthiazole (sulfurol), 1,3-benzothiazole, 1,3-thiazolidine, 2-methyl-1,3- thiazolidine, 2-isopropyl-1,3-thiazolidine,2-methylpyrazine, 2-ethylpyrazine, 2-propylpyrazine, 2-isopropylpyrazine, 2-methoxypyrazine, 2,3-dimethylpyrazine, 2,5-dimethylpyrazine, 2,6-dimethylpyrazine, 2,3,5-trimethylpyrazine, ...

13
[ 623-03-0 ]
[ 13925-00-3 ]
6-(4-chlorophenyl)-7-methyl-[5H]pyrrolo[2,3-b]pyrazine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 222 - 236.

14
[ 13925-00-3 ]
[ 2024-83-1 ]
6-(3,4-methoxyphenyl)-7-methyl-[5H]pyrrolo[2,3-b]pyrazine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 222 - 236.

15
[ 13925-00-3 ]
[ 874-90-8 ]
6-(4-methoxyphenyl)-7-methyl[5H]pyrrolo[2,3-b]-pyrazine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 222 - 236.

16
[ 13925-00-3 ]
2-(4-chlorophenyl)cyclopropane-1-carbonitrile [ No CAS ]
6-[1-(4-chloro-phenyl)-cyclopropyl]-7-methyl-5<i>H</i>-pyrrolo[2,3-<i>b</i>]pyrazine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 222 - 236.

17
[ 13925-00-3 ]
4-cyanophenyl dimethylsulfamate [ No CAS ]
6-(4-dimethylaminosulfamoyloxyphenyl)-7-methyl-[5H]pyrrolo[2,3-b]pyrazine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 222 - 236.

18
[ 13925-00-3 ]
[ 354-65-4 ]
1,1,2,2-tetrafluoro-1,2-diiodo-ethane; compound with 2-ethyl-pyrazine [ No CAS ]

References: [1]New Journal of Chemistry,2003,vol. 27,p. 1522 - 1527.

19
[ 13925-00-3 ]
[ 98-96-4 ]

References: [1]Journal of Chemical Thermodynamics,2005,vol. 37,p. 49 - 53.

20
[ 13925-00-3 ]
[ 6164-79-0 ]

References: [1]Journal of Chemical Thermodynamics,2005,vol. 37,p. 49 - 53.

21
[ 13925-00-3 ]
6-(4-hydroxyphenyl)-7-methyl[5H]pyrrolo[2,3-b]pyrazine hydrobromide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 222 - 236.

22
[ 13925-00-3 ]
2-(1'-ethoxyethyl)pyrazine [ No CAS ]

References: [1]Agricultural and Biological Chemistry,1983,vol. 47,p. 729 - 738.

23
[ 13925-00-3 ]
16,17,18,19,28,29-hexahydro-4-O-acetyl-11-acetoxy-3-[2-ethyl-4-(2,4,6-trimethylbenzyl)-piperazin-1-yl]-8-O-pivaloyl-1-deoxy-11,15-dideoxo-1,15-oxy-rifamycin [ No CAS ]
[ 13961-37-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; acetic acid; In ethanol; dichloromethane;	EXAMPLE 41 In the same manner as outlined in Examples 15 and 20, 3-[2-ethyl-4-(2,4,6-tri-methylbenzyl)-piperazin-1-yl]-8-O-pivaloyl-1-deoxy-15-deoxo-1,15-oxy-rifamycin SV, (isomer A), mp 125°-128°, is converted to 16,17,18,19,28,29-hexahydro-4-O-acetyl-11-acetoxy-3-[2-ethyl-4-(2,4,6-trimethylbenzyl)-piperazin-1-yl]-8-O-pivaloyl-1-deoxy-11,15-dideoxo-1,15-oxy-rifamycin SV, mp 152°-155°, MW: 1100 (found: MS); C62 H89 N3 O14. The starting material can be prepared, for example, in the following way: A mixture of <strong>[13925-00-3]2-<strong>[13925-00-3]ethylpyrazine</strong></strong> (15 g), platinum oxide (800 mg), ethanol (150 ml) and acetic acid (1.5 g) is hydrogenated at 45 psi for 8 hours at room temperature. It is filtered and the filtrate concentrated to an oil which is taken up in methylene chloride, treated with sodium carbonate for 0.5 hour, filtered and concentrated to dryness to white solid 2-ethylpiperazine, mp 56°-57°.

References: [1]Patent: US5180718,1993,A .

24
[ 13925-00-3 ]
[ 1126-46-1 ]
[ 83227-47-8 ]

Yield	Reaction Conditions	Operation in experiment
		from <strong>[13925-00-3]2-<strong>[13925-00-3]ethylpyrazine</strong></strong> and methyl 4-chlorobenzoate there is obtained 4'-chloro-2-(2-pyrazinyl)-propiophenone, m.p. 85°;

References: [1]Patent: US4605656,1986,A .

25
[ 13925-00-3 ]
[ 35112-28-8 ]
[ 83227-48-9 ]

Yield	Reaction Conditions	Operation in experiment
		from <strong>[13925-00-3]2-<strong>[13925-00-3]ethylpyrazine</strong></strong> and methyl 2,4-dichlorobenzoate there is obtained 2',4'-dichloro-2-(2-pyrazinyl)-propiophenone as an oil.

References: [1]Patent: US4605656,1986,A .

26
[ 13925-00-3 ]
[ 94777-52-3 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; potassium carbonate; dibenzoyl peroxide; In tetrachloromethane;	EXAMPLE 1 2-(1-Hydroxyethyl)pyrazine (100) 21.6 g of <strong>[13925-00-3]2-<strong>[13925-00-3]ethylpyrazine</strong></strong> (101) was dissolved in 300 ml of carbon tetrachloride and 35.6 g of N-bromosuccinimide added; J. Org. Chem., 37, 511(1972). The mixture was heated to 75° C. and 1.5 g of dibenzoyl peroxide was added in one portion. Heating was continued for 4 hours after which the mixture was cooled and filtered into 500 ml of a 10percent potassium carbonate solution. This mixture was rapidly stirred until no 2-(1-bromoethyl)pyrazine remained (TLC silica gel/1:1 ethyl aqueous solution was acidified to pH 6, concentrated to 200 ml and continuously extracted with ethyl acetate for two days. The ethyl acetate was removed at reduced pressure and the residue distilled, giving 18.6 g of product (100). b.p. 112°-3° (13 mm). UV H2 O max: 264 (3.85), 268 (3.82). 13 C NMR: 159.75, S(C2); 144.52, D, 143.99, D, 142.51, D (C3, C5, C6); 69.20, D (CHOH); 23.11, Q (CH3).

References: [1]Patent: US4638005,1987,A .

27
[ 13925-00-3 ]
2-(1-sulfonylethyl)pyrazine sodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; sodium sulfite; dibenzoyl peroxide; In methanol; tetrachloromethane; water;	EXAMPLE 23 2-(1-Sulfonylethyl)pyrazine sodium salt (2300) 5.4 g of <strong>[13925-00-3]2-<strong>[13925-00-3]ethylpyrazine</strong></strong> was dissolved in 100 ml of carbon tetrachloride and 8.9 g of N-bromosuccinimide added. This mixture was heated to 70°-5° C., 0.5 g dibenzoyl peroxide added and the mixture refluxed for 3 hours. It was then cooled, filtered and the filtrate concentrated in vacuo. To the resultant oil was added 10 g of sodium sulfite/100ml of water and the mixture refluxed for 3 days. It was then cooled, washed with chloroform and freeze-dried. The resultant solid was taken up in 200 ml of methanol, filtered and the filtrate concentrated. It was purified by gel permeation chromatography (Biogel P-2/water) and freeze-dried to give 9.2 g product (2300). It was recrystallized from methanol, m.p. 258°-62°. UV H2 O max: 203 (3.90), 267 (3.87), 272 (3.85). 13 C NMR: 153.54, S (C2); 145.76, D, 144.97, D, 144.14, D (C3, C5, C6); 61.14, D (--CH--); 15.18, Q (CH3).

References: [1]Patent: US4638005,1987,A .

28
[ 13925-00-3 ]
[ 132-16-1 ]
[ 86502-89-8 ]

References: [1]Chemische Berichte,1983,vol. 116,p. 2088 - 2108.

29
[ 13925-00-3 ]
[ 27636-56-2 ]
[ 99547-54-3 ]

References: [1]Inorganic Chemistry,1986,vol. 25,p. 103 - 107.

30
[ 13925-00-3 ]
silver hexafluoroantimonate [ No CAS ]
[ 321699-42-7 ]
[Ag₂(2-ethpyz)3][SbF₆]2 [ No CAS ]

References: [1]Journal of the Chemical Society, Dalton Transactions,2000,p. 3821 - 3827.

31
[ 13925-00-3 ]
potassium cyanide [ No CAS ]
copper(l) cyanide [ No CAS ]
Cu₂(cyanide)2(ethylpyrazine) [ No CAS ]

References: [1]Journal of the Chemical Society, Dalton Transactions,2001,p. 2567 - 2580.

32
[ 13925-00-3 ]
[ 7787-70-4 ]
[Cu3Br3(μ2-2-ethylpyrazine-N,N')2] [ No CAS ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2002,vol. 57,p. 1133 - 1140.

33
[ 13925-00-3 ]
[ 7787-70-4 ]
[Cu2Br2(μ2-2-ethylpyrazine-N,N')] [ No CAS ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2002,vol. 57,p. 1133 - 1140.

34
[ 13925-00-3 ]
copper(l) chloride [ No CAS ]
catena[Cu3Cl3(μ2-2-ethylpyrazine-N,N')2] [ No CAS ]

References: [1]Journal of Solid State Chemistry,2002,vol. 169,p. 103 - 112.
[2]Zeitschrift fur Anorganische und Allgemeine Chemie,.
Zeitschrift fuer Anorganische und Allgemeine Chemie,2002,vol. 628,p. 2228 - 2228.

35
[ 13925-00-3 ]
copper(l) chloride [ No CAS ]
catena[Cu3Cl3(μ2-2-ethylpyrazine-N,N')2] [ No CAS ]
poly[Cu2Cl2(μ2-2-ethylpyrazine-N,N')] [ No CAS ]

References: [1]Journal of Solid State Chemistry,2002,vol. 169,p. 103 - 112.

36
[ 13925-00-3 ]
copper(l) chloride [ No CAS ]
[ 511256-44-3 ]

37
[ 13925-00-3 ]
copper(l) chloride [ No CAS ]
poly[Cu2Cl2(μ2-2-ethylpyrazine-N,N')] [ No CAS ]

38
[ 13925-00-3 ]
silver(I) iodide [ No CAS ]
[ 928627-29-6 ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2006,vol. 61,p. 517 - 520.

39
[ 13925-00-3 ]
sodium azide [ No CAS ]
manganese (II) nitrate tetrahydrate [ No CAS ]
[Mn(N₃)2(ethylpyrazine)(H₂O)](n) [ No CAS ]

References: [1]Inorganic Chemistry,2006,vol. 45,p. 868 - 876.

40
[ 13925-00-3 ]
[ 24424-99-5 ]
[ 1104643-34-6 ]

References: [1]Tetrahedron,2009,vol. 65,p. 134 - 138.

41
[ 13925-00-3 ]
[ 3409-21-0 ]
[ 867035-87-8 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of LDA (1 mL, 2 N solution in THF, 2 mmol) in Et20 (5 mL) at 0 °C, <strong>[13925-00-3]2-<strong>[13925-00-3]ethylpyrazine</strong></strong> (238 mg, 2.2 mmol) in Et2O (1 mL) was added slowly, and the reaction mixture was stirred at 0 °C for 30 minutes. A solution of 2-(2-dimethylamino- ethyl) -indan-1-one 2b (203 mg, 1 mmol) in Et20 (1 mL) was added. The resultant mixture was stirred at 0 °C for two hours. A small piece of chip ice was added to quench the reaction. The mixture was extracted with Et20, washed with NaHC03 aqueous solution, then extracted with 20percent HCI (2 x 5 mL). The combined HCI layers were heated to 100 °C for 1 hour. After cooling to room temperature, the mixture was neutralized with cooled NH40H and extracted with EtOAc. The organic layer was dried over Na2S04 and concentrated to give dimethyl- (2- [3 -( 1 -pyrazin-2-yl-ethyl)- I H-inden-2-yl] -ethyl ) amine 4-1 as a red oil which was purified by HPLC yielding the TFA salt. Chiral HPLC separation on 4-1 using a Chiraltech Chiralpak AD-H column and hexane: isopropyl alcohol 99: 1 (with 0.1 percent isopropylamine) as elutant yielded enantiomers 4-5 and 4-6. The following compounds were made according to this procedure: No. R1 R2b R3 MW MH+ tR (method) 4-1 Pyrazin-2-yl CH3 H 293.41 294.2 3.700 (2) 4-2 Pyrimidin-4-yl CH3 H 293.41 294.0 3.997 (2) 4-3 Pyrazin-2-yl H H 279.38 280.0 3.441 (2) 4-4 3-methoxy- CH3 H 323.44 324.1 4.602 (2) pyrazin-2-yl 4-5 Pyrazin-2-yl (S) -CH3 profile 1 H 293.41 294.1 4.091 (2) 4-6 Pyrazin-2-yl (R) -CH3 profile 1 H 293.41 294.1 4.057 (2) 4-7 3-methoxy- (R) -CH3 H 323.44 323.9 4.443 (2) pyrazin-2-y1 profile 2 4-8 3-methoxy- (S) -CH3 H 323.44 323.9 4.425 (2) pyrazm-2-yl profile 4-9 3-methyl-pyrazin-2-yl H H 293.41 294.0 3.530 (2) 4-10 pyridazin-3-yl H H 279.38 280.0 3.023 (2) 4-11 3-methoxy- H H 309.41 310.0 4.279 (2) pyrazm-2-yl 4-12 pyrazin-2-yl CH3, H 307.44 308.1 3.883 (2) 4-13 5-methyl-pyrazin- 2-yl H H 293.41 294.0 3.823 (2) No. R1 R2b R3 MW MH+ tR 4-14 6-methyl-pyrazin- H H 293.41 294.0 3.801 (2) 4-15 pyrimidin-2-yl H H 279.38 280.0 3.323 (2) 4-16 3-ethoxy-pyrazin- H H 323.44 323.9 4.861 (2) 4-17 6-propoxy- H H 337.46 337.9 5.300 (2) pyrazin-2-yl 4-18 pyrazin-2-yl H Cl 313.83 314.0 4.223 (2) 4-19 3-methoxy- H Cl 343.86 344.1 18.71 (3) pyrazm-2-yl 4-20 3-methoxy- CH3 Cl 357.88 358.1 19.66 (3) pyrazm-2-yl 4-21 pyridazin-3-yl H Cl 313.83 313.8 4.027 (2) 4-22 3-inethoxy- (S) -CH3 Cl 357.88 357.8 5.195 (2) pyrazin-2-yl profile 3 4-23 3-methoxy- profile Cl 357.88 357.8 5.177 (2) pyrazin-2-yl profile 4-24 pyrazin-2-yl H CH3 293.41 293.9 4.008 (2) 4-25 pyridazin-3-yl H CH3 293.41 294.1 3.862 (2) 4-26 pyrazin-2-yl CH3 CH3 307.44 307.9 4.366 (2) 4-27 3-methoxy- CH3 CH3 337.46 337.9 5.113 (2) pyrazin-2-yl 4-28 pyrazin-2-yl (R) -CH3 CH3 307.44 307.9 4.337 (2) profile 4 4-29 pyrazin-2-yl (S) -CH3 CH3 307.44 307.9 4.336 (2) profile 4 4-30 3-methoxy- (R) -CH3 CH3 337.46 337.9 5.087 (2) pyrazin-2-yl profile 4-31 3-methoxy- profile CH3 337.46 337.9 5.100 (2) pyrazin-2-yl profile 4-32 pyrazin-2-yl H F 297.38 297.9 3.706 (2) 4-33 pyridazin-3-yl H F 297.38 297.9 3.308 (2) 4-34 3-methoxy- H F 327.40 327.9 4.558 (2) pyrazin-2-yl 4-35 3-methoxy- Me F 341.43 341.9 4.833 (2) No. R1 RZb R3 MW MH+ tR (method) 4-36 3-methoxy- (R)-CH3 F 341.43 341.9 4.919 (2) pyrazin-2-yl profile 6 4-37 3-methoxy- (S)-CH3 F 341.43 341.8 4.878 (2) pyrazm-2-yl profile 6 4-38 3-ethoxy-pyrazin- Me F 355.45 356.1 5.212 (2) -Y 4-39 3-methoxy- Et 355.45 356.1 5.294 (2) pyrazm-2-yi 4-40 pyrazin-2-yl H OCH3 309.41 310.1 3.415 (2) 4-41 pyrazin-2-yl Me OCH3 323.44 323.9 3.947 (2) 4-42 pyridazin-3-yl H OCH3 309.41 309.9 3.253 (2) 4-43 3-methoxy- Me OCH3 353.46 353.9 4.565 (2) pyrazin-2-yl 4-44 3-methoxy- (S)-CH3 OCH3 353.46 354.1 4.563 (2) pyrazm-2-yl profile 7 4-45 3-methoxy- (R)-CH3 OCH3 353.46 354.1 4.533 (2) pyrazm-2-yl profile 7 4-46 pyrazin-2-yl (R) -CH3 OCH3 323.44 323.9 3.710 (2) profile 4-47 pyrazin-2-yl (S) -CH3 profile 7 OCH3 323.44 323.9 3.774 (2) profile 4-48 3-hydroxy- CH3 309.4 310.1 3.657(2) pyrazin-2-yl 4-49 3-hydroxy- (R)-CH3 F 327.4 328.0 3.941 (2) pyrazin-2-yl 4-50 3-ethoxy-pyrazin- (R)-CH3 F 355.45 356.1 5.261 (2) 2-yl profile 4 4-51 3-ethoxy-pyrazin- (S)-CH3 F 355.45 356.1 5.286 (2) 2-yl profile 4

References: [1]Patent: WO2005/97093,2005,A1 .Location in patent: Page/Page column 34-37.
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 5307 - 5310.

42
[ 13925-00-3 ]
[ 867038-22-0 ]
2-{1-[2-(2-azetidin-1-yl-ethyl)-5-methoxy-3H-inden-1-yl]-ethyl}-pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of (5-methoxy-1-oxo-indan-2-yl) -acetic acid 19a.1 (1 g, 4.5 mmol), EDCI (949 mg, 5 mmol), HOBt (1.5 g, 11.3 mmol) and DIEA (1.7 mL, 9 mmol) in 20 mL dichloromethane was stirred at room temperature for 30 min. Pyrrolidine (483 mg, 6.8 mmol) was added and the resulting reaction mixture was stirred at room temperature for 2 hr. Water was added and the organic layer separated, dried over MgS04, filtered and concentrated to afford 5-methoxy-2-(2-oxo-2-pyrrolidin-l-yl-ethyl)-indan-l-one 21a in 61 percent yield. (MH+ = 274) A solution of s-methoxy-2- (2- oxo-2-pyrrolidin- I -yl-ethyl)-indan- I -one 21a (700 mg, 2.56 mmol) in 5mL of THF and 2 mL of dichloromethane was added dropwise to a mixture of LiAlH4 (150 mg, 3.9 mmol) in 5 mL THF at 0 °C. The resulting reaction mixture was stirred for 20 min and then refluxed for 3 hrs. The reaction mixture was cooled to room temperature and carefully quenched by the sequential addition of H2O, 15percent NaOH and H20. The mixture was stirred for half an hour, and the solid was filtered off using a celite pad and washed with excess THF. The combined filtrates were dried over MgS04 and concentrated to afford 5-methoxy-2-(2-pyrrolidin-1-yl-ethyl)-indan-1-ol 21b as a white solid (421 mg, 63percent yield). (MH+ = 262.1) A mixture of 5-methoxy-2- (2-pyrrolidin-1-yl-ethyl)-indan-1-ol 21b(400 mg, 1.5 mmol), diphenylmethanone (1.4 g, 1.5 mmol) and KOtBu (421 mg, 3.8 mmol) in toluene (10 mL) was heated at 120 °C under N2 atmosphere for 3 hrs. The cooled mixture was poured into ice (10 g) and extracted with 10percent HCI until the HCI solution was colorless. The combined acid extracts were washed with EtOAc and added dropwise with stirring into 28percent NH40H (10 mL) and ice. This basic solution was extracted with EtOAc (3 x 10 mL). The combined organic layers were washed with brine, dried over MgS04 and concentrated to give 5-methoxy-2-(2-pyrrolidin-1-yl-ethyl)-indan-1-one 21c as an oil (240 mg, 62percent yield). (MH+ = 260) Alternatively the oxidation from the substituted indan-1 -ol to the substituted indan-1-one may use chromium (VI) oxide as reagent. A mixture of pyridine (1.5 mL) and dichloromethane (25 mL) was stirred at 0°C for 15 min. Chromium (VI) oxide (900 mg, 9 mmol) was added and the mixture was stirred for an additional 15 min at 0 °C, allowed to warm to room temperature and stirred for an additional hour at room temperature. A solution of2-[2-(3,3-difluoro-pyrrolidin-l-yl)-ethyl]-indan-l-ol (405 mg, 1.5 mmol) was added and stirring continued for 15 min. After decanting, the dichloromethane layer was washed with water and dried over MgS04. Upon concentration 301 mg of the 2-[2-(3,3- difluoro-pyrrolidin-1-yl) -ethyl]-indan-1-one was obtained as an oil (76percent) and used in the next step without further purification. (MH(at) = 266) A solution of <strong>[13925-00-3]2-<strong>[13925-00-3]ethylpyrazine</strong></strong> (100 mg, 0.9 mmol) in THF (2 mL) was added dropwise to a mixture of LDA (0.41 mL, 0.82 mmol, 2M) in THF (3 mL)at 0 °C. A solution of 5-methoxy-2-(2-pyrrolidin-1-yl-ethyl)-indan-1-one 21c (100 mg, 0.41 mmol) in THF (2 mL) was added dropwise and the resulting mixture was stirred at 0 °C for 1 hr. Water (10 mL) was added to quench the reaction followed by EtOAc (10 mL) and NH40H (10 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (3 x 3mL). The combined organic layers were concentrated and the residue was dissolved in 4 mL of 20percent HCI and the resulting mixture was stirred at room temperature for 2 hours. The mixture was then poured onto 10 g of ice and 4 mL of NH40H was added dropwise. The resulting mixture was stirred and allowed to warm to room temperature. The organic layer was separated and the aqueous layer was extracted with EtOAc (3x). The combined organic layers were dried over MgS04 and concentrated. Preparative HPLC chromatography afforded 2- {1 1-[2-(2-azetidin-1-yl-ethyl)-5-methoxy-3H-inden-1-yl]-ethyl}- pyrazine 21-1. (MH+=336.1) The following compounds were made according to this procedure: No R3 R1 NR5aR5b R2b MW MH+ (method 2) 21-1 OCH3 Pyrazin-2- yl Azetidin-1-yl CH3 335.45 336.1 3.947 21-2 OCH3 Pyrazin-2- Azetidin-1-yl (R) CH3 335.45 336.1 3.941 yl Profile 7 21-3 OCH3 Pyrazin-2- Azetidin-1-yl (S) _CH3 335.45 336.1 3.974 yl Profile? 21-4 OCH3 Pyrazin-2- yl Pyrroydin-1- yl CH3 349.48 350.1 4.960 21-5 OCH3 Pyrazin-2-yl Pyrrolidin-1- yl H 335.45 336.1 3.749 21-6 OCH3 Pyridazin- Pyrrolidin-1- 335.45 336.1 3.500 3-yl yl 21-7 Pyrazin-2- Pyrrolidin-1- 305.42 306.1 3.673 yl yl 21-8 Pyridazin- Pyrrolidin-l- H 305.42 306.1 3.473 3-yl yl 21-9 OCH3 Pyrazin-2- Morpholin-4- H 351.45 352.1 3.610 yl yl 21- 10 H Pyrazin-2- (at)etidin-1-yl H 291.40 292.1 3.585 21- Pyrazin-2- 3,3-Difluoro- H 309.4 310 3.605 11 yl pyrrolidin-1-yl 21- Pyrazin-2- 3-Fluoro- 341.1 342.1 3.868 12 yl azetidin-1-yl 341.1 342.1 3.868

References: [1]Patent: WO2005/97093,2005,A1 .Location in patent: Page/Page column 58-60.

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CAS No.: 13925-00-3

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CAS No.: 13925-00-3

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[ 13925-00-3 ] Synthesis Path-Downstream 1~42

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