1H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chloride → 2-(4-tert-butyl-3,5-difluorophenoxy)-N-((1R)-1-{4-[(methylsulfonyl)amino]phenyl}ethyl)acetamide

HRID 230589

Reaction equation

HRID 230589 reaction equation
[C:1]([C:5]1[C:15]([F:16])=[CH:14][C:8]([O:9][CH2:10][C:11]([OH:13])=O)=[CH:7][C:6]=1[F:17])([CH3:4])([CH3:3])[CH3:2].[Cl-].ClC1N(C)CC[NH+]1C.Cl.[NH2:28][C@@H:29]([C:31]1[CH:36]=[CH:35][C:34]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])=[CH:33][CH:32]=1)[CH3:30]>C(N(CC)CC)C>[C:1]([C:5]1[C:6]([F:17])=[CH:7][C:8]([O:9][CH2:10][C:11]([NH:28][C@@H:29]([C:31]2[CH:32]=[CH:33][C:34]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])=[CH:35][CH:36]=2)[CH3:30])=[O:13])=[CH:14][C:15]=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 66978143N-{4-[(1R)-1-aminoethyl]phenyl}methanesulfonamide hydrochlorideHCID 68804332(4-tert-Butyl-3,5-difluorophenoxy)acetic acid

Product 1

HCID 577629162-(4-tert-butyl-3,5-difluorophenoxy)-N-((1R)-1-{4-[(methylsulfonyl)amino]phenyl}ethyl)acetamideYield 63.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

((4-tert-Butyl-3,5-difluorophenoxy)acetic acid (147 mg, 0.60 mmol), 2-chloro-1,3-dimethylimidazolinium chloride (CDI) (102 mg, 0.63 mmol), triethylamine (0.5 ml) and N-{4-[(1R)-1-aminoethyl]phenyl}methanesulfonamide hydrochloride (150 mg, 0.60 mmol) were mixed by the same procedure as described in Example 1(e) to give 167 mg (63%) of the title compound as a white solid.

Sources & evidence

ORD record
ord-e9963e10408141e08e969ae1b608a81f
Source dataset
uspto-grants-2009_07
Patent number
US07566739B2

Linked notes

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