Anisole → HCID 178441706, compound

HRID 893600Notes

Reaction equation

HRID 893600 reaction equation
C(NS(C1C=CC=CC=1C1C=CC(C[N:22]2[C:26]([C:27]([O:29][CH3:30])=[O:28])=[C:25]([Cl:31])[N:24]=[C:23]2[CH2:32][CH2:33][CH2:34][CH3:35])=CC=1)(=O)=O)(C)(C)C.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[CH2:32]([C:23]1[NH:22][C:26]([C:27]([O:29][CH3:30])=[O:28])=[C:25]([Cl:31])[N:24]=1)[CH2:33][CH2:34][CH3:35]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 86745954HCID 86745954, compound

Product 1

HCID 178441706HCID 178441706, compoundYield 214.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-((2'-((tert-butylamino)sulfonyl)(1,1'-biphenyl)-4-yl)methyl)-2-butyl-4-chloro-1H-imidazole-5-carboxylic acid, methyl ester (75.0 mg, 0.145 mmol) was stirred in trifluoroacetic acid (1.0 ml) containing anisole (20 μl) under nitrogen at room temperature for 24 hours. The trifluoroacetic acid was removed in vacuo and the residue chromatographed (silica gel, 35% ethyl acetate-hexane) to afford 1-((2'-aminosulfonyl)(1,1'-biphenyl)-4-yl)methyl)-2-butyl-4-chloro-1H-imidazole-5-carboxylic acid, methyl ester (67.5 mg, 100%) as a white solid; 1H NMR (300 MHz, CD3OD/CDCl3) δ8.08 (d, J=7.7 Hz, 1H), 7.54 (t, J=7.7 Hz, 1H), 7.46 (t, J=7.7 Hz, 1H), 7.40 (d, J=8.1 Hz, 2H), 7.26 (d, J=7.7 Hz, 1H), 7.04 (d, J=8.1 Hz, 2H), 5.57 (s, 2H), 3.80 (s, 3H), 2.64 (t, J=7.4 Hz, 2H), 1.62 (quin, J=7.4 Hz, 2H), 1.31 (sext, J=7.4 Hz, 2H), 0.89 (t, J=7.4 Hz, 3H).

Workup

  1. customThe trifluoroacetic acid was removed in vacuo
  2. customthe residue chromatographed (silica gel, 35% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-b1242c585ae64f37ba41f003916f82fe
Source dataset
uspto-grants-1992_06
Patent number
US05126342

Reaction notes

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