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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
2-Ethylpyrazine is an endogenous metabolite.
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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 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H225-H302 |
Precautionary Statements: | P210-P233-P240-P241-P242-P301+P312 |
Class: | 3 |
UN#: | 1993 |
Packing Group: | Ⅲ |
* 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.
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, ... |
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°. |
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°; |
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. |
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). |
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). |