Trifluoroacetic acid → 2-[1-(2-chlorophenyl)-1-methylethyl]-1-[3'-(methylsulfonyl)biphenyl-4-yl]-4-pyrrolidin-2-yl-1H-imidazole

HRID 1673027Notes

Reaction equation

HRID 1673027 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:11]1[N:12]([C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([S:40]([CH3:43])(=[O:42])=[O:41])[CH:35]=3)=[CH:30][CH:29]=2)[CH:13]=[C:14]([CH:16]2[CH2:20][CH2:19][CH2:18][N:17]2C(OC(C)(C)C)=O)[N:15]=1)([CH3:10])[CH3:9].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:11]1[N:12]([C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([S:40]([CH3:43])(=[O:42])=[O:41])[CH:35]=3)=[CH:30][CH:29]=2)[CH:13]=[C:14]([CH:16]2[CH2:20][CH2:19][CH2:18][NH:17]2)[N:15]=1)([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 441772841,1-dimethylethyl 2-{2-[1-(2-chlorophenyl)-1-methylethyl]-1-[3'-(methylsulfonyl)biphenyl-4-yl]-1H-imidazol-4-yl}pyrrolidine-1-carboxylate

Product 1

HCID 441772852-[1-(2-chlorophenyl)-1-methylethyl]-1-[3'-(methylsulfonyl)biphenyl-4-yl]-4-pyrrolidin-2-yl-1H-imidazoleYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,1-dimethylethyl 2-{2-[1-(2-chlorophenyl)-1-methylethyl]-1-[3′-(methylsulfonyl)biphenyl-4-yl]-1H-imidazol-4-yl}pyrrolidine-1-carboxylate (200 mg) and 5 mL of 50% TFA in DCM was stirred at room temperature for 20 min. After concentrated in vacuo, the reaction mixture was separated by prep HPLC to give 2-[1-(2-chlorophenyl)-1-methylethyl]-1-[3′-(methylsulfonyl)biphenyl-4-yl]-4-pyrrolidin-2-yl-1H-imidazole (150 mg): 1H NMR (CD3OD): δ 1.6 (m, 3H,), 1.8 (m, 1H), 1.9 (s, 3H), 2.2-2.6 (m, 4H), 3.2 (s, 3H), 3.4 (m, 2H), 4.7 (m, 1H), 7.1 (m, 1H), 7.2 (m, 5H), 7.4 (s, 1H), 7.7 (m, 3H), 8.0 (m, 2H), 8.2 (m, 1H); LC/MS M+H 520 (observed).

Workup

  1. concentrationAfter concentrated in vacuo
  2. customthe reaction mixture was separated by prep HPLC

Sources & evidence

ORD record
ord-e4bc71fad5dd4f309ae5669bd0824d36
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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