1H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chloride → HCID 21097453, compound

HRID 1350879Notes

Reaction equation

HRID 1350879 reaction equation
[CH3:1][C:2]1([CH3:17])[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][C:14]([OH:16])=O)=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.[Cl-].ClC1N(C)CC[NH+]1C.Cl.[NH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])=[C:32]([F:41])[CH:31]=1>C(N(CC)CC)C>[CH3:17][C:2]1([CH3:1])[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][C:14]([NH:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])=[C:32]([F:41])[CH:31]=3)=[O:16])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 21097488HCID 21097488, compoundHCID 21097525N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochloride

Product 1

HCID 21097453HCID 21097453, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

[(4,4-Dimethyl-3,4-dihydro-2H-chromen-7-yl)oxy]acetic acid (118 mg, 0.5 mmol), 2-chloro-1,3-dimethylimidazolinium chloride (CDI) (89 mg, 0.55 mmol), triethylamine (0.33 ml) and N{4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochloride (140 mg, 0.55 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-e8a079de55834e6ca11d0e1087c3fce7
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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