Ethyl cyanoacetate → HCID 21934570, compound

HRID 1241443Notes

Reaction equation

[H-].[Na+].[C:3]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:4].I[CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]2[N:22]([CH3:23])[CH2:21][CH2:20][N:19]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:18]=2[N:31]=1>CN(C=O)C>[C:3]([CH:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]2[N:22]([CH3:23])[CH2:21][CH2:20][N:19]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:18]=2[N:31]=1)#[N:4]

Participants

Conditions

Temperature: 0 °C

Procedure

NaH (620 mg, 24.55 mmol) was suspended in DMF (203 mL) at 0° C. under N2. Ethyl cyanoacetate (2.6 mL, 24.55 mmol) was added and the resulting mixture stirred for 30 min at 0° C. Tert-butyl 6-(2-iodoethyl)-1-methyl-2,3-dihydropyrido[2,3-b]pyrazine-4(1H)-carboxylate (6.6 g, 16.37 mmol) in DMF (10 mL) was introduced to the reaction mixture and stirred for 2 hours at room temperature. The mixture was cooled to 0 and quenched with water and extracted with EtOAc (3×). The organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (silica, 90% EtOAC/Hex) to afford colorless oil (5.78 g, 91% yield). H NMR (CDCl3) δ 1.35 (q, 3H), 1.55 (s, 9H), 2.38 (m, 2H), 2.89 (t, 2H), 2.93 (s, 3H), 3.32 (t, 2H), 3.85 (t, 2H), 3.90(m, 1H), 4.30 (q, 2H), 6.85(d, 2H). LC-MS (M+H) 389.

Workup

stirringstirred for 2 hours at room temperature
temperatureThe mixture was cooled to 0
customquenched with water
extractionextracted with EtOAc (3×)
washThe organic layers were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (silica, 90% EtOAC/Hex)

Sources & evidence

ORD record: ord-96eacbfe30fc480d988965779e722b1f
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115596B2

Reaction notes

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