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

HRID 2053538Notes

Reaction equation

HRID 2053538 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, 3H), 7.55-7.250 (m, 5H), 7.05-6.85 (m, 8H), 5.48 (s, 2H), 4.55 (d, 2H); 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-747d9b0630a04376815f26c9a8d8488c
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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