2,4-Difluorophenyl isocyanate → HCID 23122009, compound

HRID 1713529Notes

Reaction equation

[CH:1]1([C:7]2([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH:11]3[CH2:12][NH:13][CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1[N:31]=[C:32]=[O:33]>C1(C)C=CC=CC=1>[CH:17]1([C:7]2([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:11]3[CH2:12][N:13]([C:32]([NH:31][C:25]4[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:24]=4[F:23])=[O:33])[CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8]2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

Conditions

Temperature: 60 °C

Procedure

1,1-Dicyclohexyl-hexahydro-3H-oxazolo[3,4-a]pyrazin-3-one (0.13 g, 0.42 mmol) was dissolved in toluene (1.5 mL). 2,4-Difluorophenyl isocyanate (0.10 g, 0.64 mmol) was added thereto, and the mixture was stirred at 60° C. for 14 hours. The reaction solution was concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:2) and crystallized from hexane to obtain the title compound (0.12 g, yield 59%).

Workup

concentrationThe reaction solution was concentrated under reduced pressure
customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:2)
customcrystallized from hexane

Sources & evidence

ORD record: ord-4d3bab73cb5d4ff3b3664c322214a160
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795267B2

Reaction notes

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