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

HRID 230588

Reaction equation

HRID 230588 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])=[C:33]([F:42])[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:36]=[CH:35][C:34]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])=[C:33]([F:42])[CH:32]=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 66841089N-{4-[(1R)-1-aminoethyl]-2-fluorophenyl}methanesulfonamide hydrochlorideHCID 68804332(4-tert-Butyl-3,5-difluorophenoxy)acetic acid

Product 1

HCID 577629232-(4-Tert-butyl-3,5-difluorophenoxy)-N-((1R)-1-{3-fluoro-4-[(methylsulfonyl)amino]phenyl}ethyl)acetamideYield 37%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

(4-tert-Butyl-3,5-difluorophenoxy)acetic acid (166 mg, 0.68 mmol), 2-chloro-1,3-dimethylimidazolinium chloride (CDI) (110 mg, 0.68 mmol), triethylamine (0.5 ml) and N-{4-[(1R)-1-aminoethyl]-2-fluorophenyl}methanesulfonamide hydrochloride (183 mg, 0.68 mmol) were mixed by the same procedure as described in Example 1(e) to give 115 mg (37%) of the title compound as a white solid.

Sources & evidence

ORD record
ord-958f5bc5e2c7406e8a469acd75604569
Source dataset
uspto-grants-2009_07
Patent number
US07566739B2

Linked notes

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