Triethylamine → [4-(4-Ethanesulfonyl-piperazine-1-carbonyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

HRID 1929580Notes

Reaction equation

HRID 1929580 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:32])[CH2:11][C:12]1[C:21]([CH3:22])=[C:20]([C:23]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[O:24])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([F:31])[CH:18]=2)[CH:13]=1.[CH2:33]([S:35](Cl)(=[O:37])=[O:36])[CH3:34].C(N(CC)CC)C>ClCCl>[CH3:8][O:9][C:10](=[O:32])[CH2:11][C:12]1[C:21]([CH3:22])=[C:20]([C:23]([N:25]2[CH2:30][CH2:29][N:28]([S:35]([CH2:33][CH3:34])(=[O:37])=[O:36])[CH2:27][CH2:26]2)=[O:24])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([F:31])[CH:18]=2)[CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 67367468[6-Fluoro-3-methyl-4-(piperazine-1-carbonyl)-naphthalen-2-yl]-acetic acid methyl ester trifluoroacetate

Product 1

HCID 59326736[4-(4-Ethanesulfonyl-piperazine-1-carbonyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl esterYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [6-fluoro-3-methyl-4-(piperazine-1-carbonyl)-naphthalen-2-yl]-acetic acid methyl ester trifluoroacetate (45.8 mg, 0.10 mmol) and ethanesulfonyl chloride (14 μL, 0.15 mmol) in dichloromethane was added triethylamine (306 μL, 2.2 mmol). The resulting mixture was stirred at room temperature overnight, and concentrated in vacuo. The residue was purified by column chromatography (gradient elution with 20-40% ethyl acetate in petroleum ether) to afford [4-(4-ethanesulfonyl-piperazine-1-carbonyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (38 mg, 87%) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography (gradient elution with 20-40% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-6ce42c9a0f0a433284e6f5c6d18e8c12
Source dataset
uspto-grants-2012_05
Patent number
US08188090B2

Reaction notes

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