1H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chloride → 2-(4-tert-Butyl-3-fluorophenoxy)-N-{3-methoxy-4-[(methylsulfonyl)amino]benzyl}acetamide

HRID 1350880Notes

Reaction equation

HRID 1350880 reaction equation
[C:1]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([OH:13])=O)=[CH:7][C:6]=1[F:16])([CH3:4])([CH3:3])[CH3:2].[Cl-].ClC1N(C)CC[NH+]1C.FC(F)(F)[C:28](O)=[O:29].[NH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([NH:41][S:42]([CH3:45])(=[O:44])=[O:43])=[CH:37][C:36]=1OC>C(N(CC)CC)C>[C:1]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([NH:33][CH2:34][C:35]2[CH:36]=[CH:37][C:38]([NH:41][S:42]([CH3:45])(=[O:43])=[O:44])=[C:39]([O:29][CH3:28])[CH:40]=2)=[O:13])=[CH:7][C:6]=1[F:16])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 21097504(4-tert-Butyl-3-fluorophenoxy)acetic acidHCID 69124640N-[4-(aminomethyl)-3-methoxyphenyl]methanesulfonamide trifluoroacetic acid

Product 1

HCID 210974632-(4-tert-Butyl-3-fluorophenoxy)-N-{3-methoxy-4-[(methylsulfonyl)amino]benzyl}acetamideYield 20%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

(4-tert-Butyl-3-fluorophenoxy)acetic acid (113 mg, 0.5 mmol), 2-chloro-1,3-dimethylimidazolinium chloride (CDI) (89 mg, 0.55 mmol), triethylamine (0.33 ml) and N-[4-(aminomethyl)-3-methoxyphenyl]methanesulfonamide trifluoroacetic acid (258 mg, 0.75 mmol) were treated in the same procedure described in Example 2(b). The crude residue was applied to a silica gel chromatography column and eluted with a volume mixture of hexane and ethyl acetate (3/1 to 1/1) to furnish 43 mg (20% yield) of the title compound as a white solid.

Workup

  1. washeluted with a volume mixture of hexane and ethyl acetate (3/1 to 1/1)

Sources & evidence

ORD record
ord-e26d44f64d1548209a56230dc778143b
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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