Benzylamine → tert-butyl (4S,5R)-2-(benzylamino)-4,5-bis(4-fluorophenyl)-4,5-dihydroimidazole-1-carboxylate

HRID 2053537Notes

Reaction equation

HRID 2053537 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:10](SC)=[N:9]2)=[CH:4][CH:3]=1.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CO>[C:16]([O:15][C:13]([N:11]1[C@H:12]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:9]=[C:10]1[NH:29][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 865963234-Fluorophenyl-2-methylthio-4,5-dihydro-imidazole-1-carboxylic Acid, Tert-Butyl Ester

Product 1

HCID 68570645tert-butyl (4S,5R)-2-(benzylamino)-4,5-bis(4-fluorophenyl)-4,5-dihydroimidazole-1-carboxylateYield 123.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of intermediate 62 (0.5 g, 1.24 mmol), benzylamine (0.680 mL, 6.2 mmol) and MeOH (0.1 mL) is heated at 100° C. overnight. The reaction mixture is cooled to RT and purified by chromatography on silica gel; gradient elution with heptane:EtOAc (75:25-60:40) gives 0.354 g of the product 160. 1H NMR (CDCl3) δ 7.55-7.25 (m, 6H), 6.95-6.85 (m, 2H), 6.80-6.60 (m, 6H), 5.45-5.20 (m, 2H), 4.75-4.55 (m, 2H), 1.16 (s, 9H)

Workup

  1. temperatureThe reaction mixture is cooled to RT
  2. custompurified by chromatography on silica gel
  3. washgradient elution with heptane:EtOAc (75:25-60:40)

Sources & evidence

ORD record
ord-250e502e6348426e9c79db3af48933db
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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