Acetonitrile → 4-(1-acetylpyrrolidin-2-yl)-2-[1-(2-chlorophenyl)-1-methylethyl]-1-[3'-(methylsulfonyl)biphenyl-4-yl]-1H-imidazole

HRID 1673029Notes

Reaction equation

HRID 1673029 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:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:28]=3)=[CH:23][CH:22]=2)[CH:13]=[C:14]([CH:16]2[CH2:20][CH2:19][CH2:18][NH:17]2)[N:15]=1)([CH3:10])[CH3:9].C(#N)C.[C:40](OC(=O)C)(=[O:42])[CH3:41]>N1C=CC=CC=1>[C:40]([N:17]1[CH2:18][CH2:19][CH2:20][CH:16]1[C:14]1[N:15]=[C:11]([C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])([CH3:10])[CH3:9])[N:12]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:28]=3)=[CH:23][CH:22]=2)[CH:13]=1)(=[O:42])[CH3:41]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 7918Acetic AnhydrideHCID 441772852-[1-(2-chlorophenyl)-1-methylethyl]-1-[3'-(methylsulfonyl)biphenyl-4-yl]-4-pyrrolidin-2-yl-1H-imidazole

Product 1

HCID 441772874-(1-acetylpyrrolidin-2-yl)-2-[1-(2-chlorophenyl)-1-methylethyl]-1-[3'-(methylsulfonyl)biphenyl-4-yl]-1H-imidazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-[1-(2-chlorophenyl)-1-methylethyl]-1-[3′-(methylsulfonyl)biphenyl-4-yl]-4-pyrrolidin-2-yl-1H-imidazole, acetonitrile and pyridine was added acetic anhydride. The solution was heated to reflux for 1 h. After a routine aqueous work up, the crude product was purified by prep HPLC to give 4-(1-acetylpyrrolidin-2-yl)-2-[1-(2-chlorophenyl)-1-methylethyl]-1-[3′-(methylsulfonyl)biphenyl-4-yl]-1H-imidazole: 1H NMR (CDCl3): δ 1.6 (m, 3H,), 1.8 (m, 1H), 1.9 (br, 2H), 2.1 (m, 4H), 2.3 (m, 2H), 3.1 (s, 3H), 3.5 (m, 1H) 3.7 (m, 1H), 4.5 (m, 1H), 5.0 (m, 1H), 6.8 (m, 2H), 7.1 (m, 5H), 7.6 (m, 2H), 7.7 (m, 1H), 7.8 (m, 1H), 7.9 (m, 1H), 8.2 (m, 1H); LC/MS M+H 562 (observed).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1 h
  3. customAfter a routine aqueous work up, the crude product was purified by prep HPLC

Sources & evidence

ORD record
ord-c540e1d8bd9049a1bec4b26845df2223
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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