Hydrochloric Acid → (4S,5R)-N-benzyl-4,5-bis(4-fluorophenyl)-4,5-dihydro-1H-imidazol-2-amine;hydrochloride

HRID 18745Notes

Reaction equation

HRID 18745 reaction equation
[ClH:1].C(OC([N:9]1[C@H:13]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C@H:12]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[N:11]=[C:10]1[NH:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=O)(C)(C)C>CCOC(C)=O>[ClH:1].[F:20][C:17]1[CH:16]=[CH:15][C:14]([C@H:13]2[C@@H:12]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[NH:11][C:10]([NH:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[N:9]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68570645tert-butyl (4S,5R)-2-(benzylamino)-4,5-bis(4-fluorophenyl)-4,5-dihydroimidazole-1-carboxylate

Product 1

HCID 68570275(4S,5R)-N-benzyl-4,5-bis(4-fluorophenyl)-4,5-dihydro-1H-imidazol-2-amine;hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Hydrogen chloride is bubbled into a solution of 160 (350 mg, 0.76 mmol) in EtOAc (20 mL) for 0.5 min, and the solution is stirred at RT overnight. The solvent is removed by rotary evaporation, and the residue is triturated with Et2O to give 230 mg of the product 161. 1H NMR (DMSO-d6) δ 9.50-8.40 (m, 3 H), 7.55-7.250 (m, 5 H), 7.05-6.85 (m, 8 H), 5.48 (s, 2 H), 4.55 (d, 2 H); MS: m/z 364 (M++1).

Workup

  1. customThe solvent is removed by rotary evaporation
  2. customthe residue is triturated with Et2O

Sources & evidence

ORD record
ord-5830f88d6ea1429dbac042024e5aeb57
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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