Carbon Dioxide → HCID 117667605, compound

HRID 1526235Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[Cl:13][C:14]1[C:15]([CH:21]2[CH2:23][CH2:22]2)=[N:16][CH:17]=[C:18]([Cl:20])[N:19]=1.[C:24](=[O:26])=[O:25].Cl>O1CCCC1>[Cl:20][C:18]1[C:17]([C:24]([OH:26])=[O:25])=[N:16][C:15]([CH:21]2[CH2:23][CH2:22]2)=[C:14]([Cl:13])[N:19]=1

Participants

Conditions

Temperature: -100 °C

Procedure

Under an argon atmosphere, to a mixture of tetrahydrofuran (6 mL) and diisopropylamine (258 μL) was added dropwise n-butyllithium (1.62 M n-hexane solution, 1.04 mL) under ice-cooling. After cooling to −100° C., a mixture of 3,5-dichloro-2-cyclopropylpyrazine (290 mg) and tetrahydrofuran (2 mL) was added dropwise thereto, followed by stirring for 10 minutes. The obtained reactant was added to dry ice (10 g) and tetrahydrofuran (5 mL), followed by stirring for 30 minutes in a water bath. To the reactant were added 1 M hydrochloric acid and a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 3,5-dichloro-6-cyclopropylpyrazine-2-carboxylic acid (350 mg) as an oily material.

Workup

temperaturecooling
additionwas added dropwise
stirringby stirring for 30 minutes in a water bath
extractiona saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate
washThe organic phase was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-3d568c78625049c1a00cbc5642f8aa83
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085540B2

Reaction notes

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