3,4,5-Trifluorobenzylamine → tert-butyl (4S,5R)-4,5-diphenyl-2-[(3,4,5-trifluorophenyl)methylamino]-4,5-dihydroimidazole-1-carboxylate

HRID 18731Notes

Reaction equation

HRID 18731 reaction equation
[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:9](SC)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:27][C:28]1[CH:29]=[C:30]([CH:33]=[C:34]([F:37])[C:35]=1[F:36])[CH2:31][NH2:32]>CO>[C:21]([O:20][C:18]([N:10]1[C@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=[C:9]1[NH:32][CH2:31][C:30]1[CH:33]=[C:34]([F:37])[C:35]([F:36])=[C:28]([F:27])[CH:29]=1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 27770483,4,5-TrifluorobenzylamineHCID 86596320cis-4,5-Diphenyl-2-methylthio-4,5-dihydro-imidazole-1-carboxylic Acid, Tert-Butyl Ester

Product 1

HCID 68568708tert-butyl (4S,5R)-4,5-diphenyl-2-[(3,4,5-trifluorophenyl)methylamino]-4,5-dihydroimidazole-1-carboxylateYield 67.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of intermediate 59 (0.5 g, 1.36 mmol), 3,4,5-trifluorobenzylamine (0.66 g, 4.0 mmol) and MeOH (0.2 mL) is heated at 100° C. for 2 days. The reaction mixture is cooled to RT, and the mixture is purified by chromatography on silica gel; gradient elution with heptane:EtOAc (70:30-50:50) gives 0.44 g of the product 83. 1H NMR (CDCl3) δ 7.59 (s, 1 H), 7.20-7.05 (m, 2 H), 7.05-6.90 (m, 8 H), 6.80-6.70 (m, 2 H), 5.45-5.30 (m, 2 H), 4.70-4.50 (m, 2 H), 1.16 (s, 9 H); MS: m/z 482 (M++1).

Workup

  1. temperatureThe reaction mixture is cooled to RT
  2. customthe mixture is purified by chromatography on silica gel
  3. washgradient elution with heptane:EtOAc (70:30-50:50)

Sources & evidence

ORD record
ord-1d2e71980bfe47228f66cf62f2ca28da
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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