2,2-Difluoro-2-phenylethylamine → HCID 12147025, compound

HRID 1836327Notes

Reaction equation

[CH3:1][CH2:2][O:3][C:4]([CH2:6][CH2:7][N:8]1[C:13]([CH3:14])=[CH:12][N:11]=[C:10](O)[C:9]1=[O:16])=[O:5].[F:17][C:18]([F:27])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:19][NH2:20]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:17][C:18]([F:27])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:19][NH:20][C:10]1[C:9](=[O:16])[N:8]([CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:13]([CH3:14])=[CH:12][N:11]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 1-[(2-ethoxycarbonyl)ethyl]-3-bromo-6-methylpyrazinone (2-6) (0.441 g, 1.6 mmol) in toluene (15 mL) was added 2,2-difluoro-2-phenylethylamine (2-10) (0.51 g, 3.2 mmol). The resulting mixture was stirred at 110° C. for 24 hours. The mixture was diluted with ethyl acetate (100 mL) and washed with 10% hydrochloric acid (20 mL) and brine (20 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography using ethyl acetate/n-hexane (1:1) as eluent to afford the title compound (0.46 g, 81%) as a pale yellow solid. Rf 0.19 (ethyl acetate/hexane 1/1); 1H-NMR (CDCl3): δ 1.26 (t, J=7.2 Hz, 3H), 2.18 (d, J=1.2 Hz, 3H), 2.66 (t, J=6.8 Hz, 2H), 4.06 (dt, J=6.8, 14.4 Hz, 2H), 4.12 (q, J=6.8 Hz, 2H), 4.18 (t, J=7.6 Hz, 2H), 6.11 (t, J=6.4 Hz, 1H), 6.61(d, J=0.8 Hz, 1H), 7.37-7.41 (m, 3H), 7.49-7.53 (m, 2H).

Workup

washwashed with 10% hydrochloric acid (20 mL) and brine (20 mL)
dry with materialThe organic phase was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe crude residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-9dd128e1d17b47e98ee35b2e203a137b
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777431B2

Reaction notes

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