1-Fluoro-4-(isocyanatomethyl)benzene → 1,1-Bis(3-fluorophenyl)-N-[(4-fluorophenyl)methyl]-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxamide

HRID 1713567Notes

Reaction equation

HRID 1713567 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)[CH:12]3[CH2:13][NH:14][CH2:15][CH2:16][N:11]3[C:10](=[O:17])[O:9]2)[CH:5]=[CH:6][CH:7]=1.[F:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][N:33]=[C:34]=[O:35])=[CH:28][CH:27]=1>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)[CH:12]3[CH2:13][N:14]([C:34]([NH:33][CH2:32][C:29]4[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=4)=[O:35])[CH2:15][CH2:16][N:11]3[C:10](=[O:17])[O:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 27333761-Fluoro-4-(isocyanatomethyl)benzeneHCID 231220271,1-Bis(3-fluorophenyl)-hexahydro-3H-oxazolo[3,4-a]pyrazin-3-one

Product 1

HCID 231220471,1-Bis(3-fluorophenyl)-N-[(4-fluorophenyl)methyl]-tetrahydro-3-oxo-3H-oxazolo[3,4-a]pyrazine-7(1H)-carboxamideYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1-Bis(3-fluorophenyl)-hexahydro-3H-oxazolo[3,4-a]pyrazin-3-one (0.18 g, 0.55 mmol) was dissolved in tetrahydrofuran (5 mL). (4-Fluorophenyl)methyl isocyanate (0.15 g, 1.0 mmol) was added thereto, and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=50:1 to ethyl acetate) to obtain the title compound (0.25 g, yield 96%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=50:1 to ethyl acetate)

Sources & evidence

ORD record
ord-2245ab1540314fb29394f357264f3835
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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