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

HRID 1350842Notes

Reaction equation

HRID 1350842 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[Cl:16])([CH3:4])([CH3:3])[CH3:2].[Cl-].ClC1N(C)CC[NH+]1C.Cl.[NH2:27][C@@H:28]([C:30]1[CH:35]=[CH:34][C:33]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])=[CH:32][CH:31]=1)[CH3:29]>C(N(CC)CC)C>[C:1]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([NH:27][C@@H:28]([C:30]2[CH:31]=[CH:32][C:33]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])=[CH:34][CH:35]=2)[CH3:29])=[O:13])=[CH:7][C:6]=1[Cl:16])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 21097497(4-tert-Butyl-3-chlorophenoxy)acetic acidHCID 66978143N-{4-[(1R)-1-aminoethyl]phenyl}methanesulfonamide hydrochloride

Product 1

HCID 116263152-(4-tert-Butyl-3-chlorophenoxy)-N-((1R)-1-{4-[(methylsulfonyl)amino]phenyl}ethyl)acetamideYield 41.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

(4-tert-Butyl-3-chlorophenoxy)acetic acid (121 mg, 0.50 mmol), 2-chloro-1,3-dimethylimidazolinium chloride (CDI) (86 mg, 0.53 mmol), triethylamine (0.5 ml) and N-{4-[(1R)-1-aminoethyl]phenyl}methanesulfonamide hydrochloride (125 mg, 0.50 mmol, Bioorganic & Medicinal Chemistry Letters, 2004, 14, 1751–1755) were treated in the same procedure described in Example 2(b) to give 91 mg (40% yield) of the titled compound as a white solid.

Sources & evidence

ORD record
ord-6576a8fa64a042a2822db2145f29e506
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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