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

HRID 1350869

Reaction equation

HRID 1350869 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[O:16][CH2:17][CH:18]1[CH2:20][CH2:19]1)([CH3:4])([CH3:3])[CH3:2].[Cl-].ClC1N(C)CC[NH+]1C.Cl.[NH2:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([NH:39][S:40]([CH3:43])(=[O:42])=[O:41])=[C:35]([F:44])[CH:34]=1>C(N(CC)CC)C>[C:1]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([NH:39][S:40]([CH3:43])(=[O:42])=[O:41])=[C:35]([F:44])[CH:34]=2)=[O:13])=[CH:7][C:6]=1[O:16][CH2:17][CH:18]1[CH2:20][CH2:19]1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 21097500[4-tert-Butyl-3-(cyclopropylmethoxy)phenoxy]acetic acidHCID 21097525N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochloride

Product 1

HCID 210974612-[4-tert-Butyl-3-(cyclopropylmethoxy)phenoxy]-N-{3-fluoro-4-[(methylsulfonyl)amino]benzyl}acetamideYield 78.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

[4-tert-Butyl-3-(cyclopropylmethoxy)phenoxy]acetic acid (139 mg, 0.5 mmol), 2-chloro-1,3-dimethylimidazolinium chloride (CDI) (89 mg, 0.6 mmol), triethylamine (0.2 ml) and N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochloride (140 mg, 0.6 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 furnish 188 mg (78% yield) of the title compound as a white solid.

Workup

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

Sources & evidence

ORD record
ord-57cd639bd7354aca9e2c5206037dd80c
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Linked notes

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