Hydrochloric Acid → (4S,5R)-4,5-diphenyl-N-[(3,4,5-trifluorophenyl)methyl]-4,5-dihydro-1H-imidazol-2-amine;hydrochloride

HRID 2053525Notes

Reaction equation

HRID 2053525 reaction equation
[ClH:1].C(OC([N:9]1[C@H:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:11]=[C:10]1[NH:26][CH2:27][C:28]1[CH:33]=[C:32]([F:34])[C:31]([F:35])=[C:30]([F:36])[CH:29]=1)=O)(C)(C)C>CCOC(C)=O>[ClH:1].[C:14]1([C@H:13]2[C@@H:12]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:11][C:10]([NH:26][CH2:27][C:28]3[CH:33]=[C:32]([F:34])[C:31]([F:35])=[C:30]([F:36])[CH:29]=3)=[N:9]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68568708tert-butyl (4S,5R)-4,5-diphenyl-2-[(3,4,5-trifluorophenyl)methylamino]-4,5-dihydroimidazole-1-carboxylate

Product 1

HCID 68570925(4S,5R)-4,5-diphenyl-N-[(3,4,5-trifluorophenyl)methyl]-4,5-dihydro-1H-imidazol-2-amine;hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Hydrogen chloride is bubbled into a solution of 83 (0.44 g, 0.91 mmol) in EtOAc (15 mL) for 1 min, and the solution is stirred at RT overnight. The solvent is removed by rotary evaporation, and the residue crystallized from dichloromethane and Et2O give 0.21 g of the product 84. 1H NMR (DMSO-d6) δ 9.40 (s, 1H), 9.14 (t, 1H), 7.88 (s, 1H), 7.20-6.80 (m, 8H), 6.80-6.55 (m, 4H), 5.07 (s, 2H), 4.70-4.50 (m, 2H); MS: m/z 382 (M++1).

Workup

  1. customThe solvent is removed by rotary evaporation
  2. customthe residue crystallized from dichloromethane and Et2O

Sources & evidence

ORD record
ord-a2b1af7fd0dc4efc947a2624b9484e5c
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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