Triethylamine → HCID 78078994, compound

HRID 1887493Notes

Reaction equation

HRID 1887493 reaction equation
Cl.[F:2][C:3]([F:21])([F:20])[O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:18][CH:17]3[CH:13]([CH2:14][NH:15][CH2:16]3)[C:12]2=[O:19])=[CH:7][CH:6]=1.[N:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=1)=[C:23]=[O:24].CCN(CC)CC>ClCCl>[F:33][C:32]([F:34])([F:35])[O:31][C:28]1[CH:27]=[CH:26][C:25]([NH:22][C:23]([N:15]2[CH2:14][CH:13]3[CH:17]([CH2:18][N:11]([C:8]4[CH:9]=[CH:10][C:5]([O:4][C:3]([F:2])([F:20])[F:21])=[CH:6][CH:7]=4)[C:12]3=[O:19])[CH2:16]2)=[O:24])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 92298p-(Trifluoromethoxy)phenyl isocyanateHCID 131730791HCID 131730791, compound

Product 1

HCID 78078994HCID 78078994, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-Trifluoromethoxy-phenyl)-hexahydro-pyrrolo[3,4-c]pyrrol-1-one, hydrochloride (0.11 g, 0.36 mmol), 1-isocyanato-4-(trifluoromethoxy)benzene (0.15 g, 0.72 mmol) and Et3N (0.15 g, 1.44 mmol) were added to dichloromethane (2 mL), the mixture was stirred at ambient temperature overnight. The mixture was concentrated under reduced pressure, purified by prep-HPLC to yield the title compound (50 mg, 28%) as white solid. 1H NMR (300 MHz, CDCl3): δ 7.68-7.65 (m, 2H), 7.42-7.40 (m, 2H), 7.39-7.13 (m, 4H), 4.18-4.03 (m, 3H), 3.79-3.69 (m, 2H), 3.45-3.38 (m, 2H), 3.22-3.20 (m, 1H); LC-MS: 489.8 [M+1]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-7fdc1da2342341dd934526e686860b61
Source dataset
uspto-grants-2013_08
Patent number
US08501768B2

Reaction notes

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