Isopropyl chloroformate → HCID 118079404, compound

HRID 1485776Notes

Reaction equation

[Br:1][C:2]1[CH:15]=[N:14][C:5]2[N:6]([C:11](=[O:13])[CH3:12])[C@@H:7]([CH3:10])[CH2:8][NH:9][C:4]=2[CH:3]=1.C(N(CC)C(C)C)(C)C.Cl[C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27]>C(OCC)(=O)C>[C:11]([N:6]1[C@@H:7]([CH3:10])[CH2:8][N:9]([C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])[C:4]2[CH:3]=[C:2]([Br:1])[CH:15]=[N:14][C:5]1=2)(=[O:13])[CH3:12]

Participants

Conditions

Temperature: 50 °C

Procedure

A reaction vial was charged with (S)-1-(7-bromo-3-methyl-2,3-dihydropyrido[2,3-b]pyrazin-4(1H)-yl)ethanone (0.054 g, 0.2 mmol) and N,N-diisopropylethylamine (0.245 mL, 1.40 mmol) was added. Isopropyl chloroformate (1.0 M solution in toluene, 1.00 mL, 1.00 mmol) was added, and the reaction was heated at 50° C. overnight. The reaction was diluted with ethyl acetate (3 mL) and washed with saturated aqueous sodium bicarbonate solution (2 mL). The aqueous layer was separated and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified via column chromatography on silica gel (eluting with 20% ethyl acetate-hexane) to afford (S)-isopropyl 4-acetyl-7-bromo-3-methyl-3,4-dihydropyrido[2,3-b]pyrazine-1(2H)-carboxylate (0.070 g, 98%) as a colorless oil. MS (ESI, pos. ion) m/z 356, 358 [M+H]+.

Workup

customA reaction
additionwas added
washwashed with saturated aqueous sodium bicarbonate solution (2 mL)
customThe aqueous layer was separated
extractionextracted with ethyl acetate
dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified via column chromatography on silica gel (eluting with 20% ethyl acetate-hexane)

Sources & evidence

ORD record: ord-90e1d1e2fcc6468aa488d2315148a1b0
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422281B2

Reaction notes

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