Imidazole → HCID 25254370, compound

HRID 219478Notes

Reaction equation

HRID 219478 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[C:10]([O:11][CH2:12][CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])=[C:9]([O:23][CH3:24])[C:8]([Cl:25])=[C:7]([CH3:26])[C:6]=1[C:27](=[O:29])[CH3:28].[NH:30]1[CH:34]=[CH:33][N:32]=[CH:31]1>C(Cl)Cl>[Cl:25][C:8]1[C:7]([CH3:26])=[C:6]([C:27](=[O:29])[CH3:28])[C:5]([O:4][CH2:3][CH2:2][N:30]2[CH:34]=[CH:33][N:32]=[CH:31]2)=[C:10]([O:11][CH2:12][CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])[C:9]=1[O:23][CH3:24]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 595835231-{2-(2-Bromo-ethoxy)-5-chloro-3-[3-(4-fluoro-phenyl)-butoxy]-4-methoxy-6-methyl-phenyl}-ethanone

Product 1

HCID 25254370HCID 25254370, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Example 8a (50 mg, 0.10 mmol) was reacted with imidazole (8.0 eq.) as described under General Procedure G and the crude mixture was dissolved in DCM and HCl gas was bubbled through it for 3 minutes. Then, solvent was removed under vacuum and the residue was suspended in dry ether and triturated to afford the title compound as a off-white solid (22 mg, 45%). 1H NMR (300 MHz, CDCl3) δ 9.57 (bs, 1H), 7.33 (bs, 1H) 7.19-7.14 (m, 3H), 7.02-6.96 (m, 2H), 4.60 (bs, 2H), 4.37 (bs, 2H), 3.89-3.76 (m, 5H), 2.88-2.93 (m, 1H), 2.32 (s, 3H), 2.16 (s, 3H), 1.94-1.96 (m, 2H), 1.27 (d, J=6.6 Hz, 3H). MS (ES+) m/z 475.2 (M+H+).

Workup

  1. customHCl gas was bubbled through it for 3 minutes
  2. customThen, solvent was removed under vacuum
  3. customtriturated

Sources & evidence

ORD record
ord-7a5c69d477f449289f0d7101793fed3d
Source dataset
uspto-grants-2012_06
Patent number
US08202513B2

Reaction notes

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