3,5-Dichloropyrazine-2-carboxyamide
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3,5-Dichloropyrazine-2-carboxyamide
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CAS No:
312736-49-5
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Formula:
C5H2Cl2N2O2
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Chemical Name:
3,5-Dichloropyrazine-2-carboxyamide
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Synonyms:
3,5-dichloropyrazine-2-carboxylic acid;Pyrazinecarboxylic acid, 3,5-dichloro-;3,5-dichloro-pyrazine-2-carboxylic acid;2-Carboxy-3,5-dichloropyrazine;SCHEMBL1615193;CTK8B4412;2-carboxy-3,5-dichloropyrazine;;DTXSID50627428;ANW-44929;EBD377129
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CAS No:
Safety Information
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
H302
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
3,5-Dichloropyrazine-2-carboxyamide Use and Manufacturing
To a solution of diisopropylamine (23.5 mL, 167.7 mmol) in THF (400 mL) at -20° C. was added n-butyllithium (1.6 M solution in hexanes, 104 mL, 166 mmol) dropwise and the reaction mixture was stirred at the same temperature for 30 minutes (min). Then the reaction mixture was cooled to -78° C. and a solution of 2, 6-dichloropyrazine (10 g, 67 mmol) in THF (400 mL) was added drop wise over a period of 1.5 hr. The reaction mixture was stirred for additional 1 hr. Then the reaction mixture was poured on to dry ice and allowed to warm to room temperature over a period of 16 hr. The reaction mixture was treated with 1.5 N HCl (200 mL) and extracted with EtOAc. The EtOAc layer was extracted with saturated sodium bicarbonate solution; the aqueous layer was acidified with 1.5 N HCl, extracted with EtOAc, washed with brine and concentrated to obtain the product as pale yellow solid. The solid thus obtained was not purified further and used as such for the next step.Yield: 9 g (69.5percent).1H NMR (300 MHz, DMSO-d6): 8.9 (s, 1H)2, 2, 6, 6-tetramethylpiperidine (2.84 g, 20.1 mmol) in THF (250 mL) at -10To a solution of diisopropylamine (13.0 niL, 92.6 mmol, 2.3 eq.) in anhydrousTHF (300 rnL) at -78°C under NTo a solution of lithium diisopropylamide (2.0 M heptane/tetrahydrofuran/ethylbenzene, 11.10 mL, 22.20 mmol) in THF (75 mL) at -78 °C was added a solution of 2, 6-dichloropyrazine (1.44 g, 9.67 mmol) in THF (20 mL) at room temperature over 20 min. The reaction mixture was stirred at -78 °C for 1.5 h and added via cannula to a 3 -neck flask containing dry ice at -78 °C. The reaction mixture was warmed from -78 °C to room temperature over 21 h and quenched with 5 M HC1. The mixture was partitioned between brine and EtOAc. The aqueous phase was acidified to pH 3.5 with 5 M HC1. The aqueous phase was extracted with EtOAc (6 x) and the combined organic extracts were washed with brine (1 x), dried over MgS0Step 1:
Computed Properties
Molecular Weight:192.98
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:191.9493327
Monoisotopic Mass:191.9493327
Topological Polar Surface Area:63.1
Heavy Atom Count:11
Complexity:167
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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3,5-Dichloropyrazine-2-carboxyamide
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