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

HRID 18744Notes

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

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, 6 H), 6.95-6.85 (m, 2 H), 6.80-6.60 (m, 6 H), 5.45-5.20 (m, 2 H), 4.75-4.55 (m, 2 H), 1.16 (s, 9 H)

Workup

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

Sources & evidence

ORD record: ord-5a306d0da0c444a7b25fbf0a86f330e8
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741493B2

Reaction notes

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