Methylamine → 2-{[6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-amino}-N-methyl-acetamide

HRID 1013599Notes

Reaction equation

HRID 1013599 reaction equation
C([O:3][C:4](=O)[CH2:5][NH:6][CH2:7][CH:8]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=3)(=[O:20])=[O:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)C.[CH3:29][NH2:30]>CO>[F:27][C:23]1[CH:22]=[C:21]([S:18]([C:14]2[CH:13]=[C:12]3[C:17](=[CH:16][CH:15]=2)[CH:8]([CH2:7][NH:6][CH2:5][C:4]([NH:30][CH3:29])=[O:3])[CH2:9][CH2:10][CH2:11]3)(=[O:20])=[O:19])[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 66651330{[6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-amino}-acetic acid ethyl ester

Product 1

HCID 666515372-{[6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-amino}-N-methyl-acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

{[6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-amino}-acetic acid ethyl ester (0.42 g) was dissolved in 20 m of 1. 1 molar methylamin in methanol. The solution was stirred at room temperature for 24 hours and then concentrated to an oil under reduced pressure. The oil was dissolved in ethanol and 1N HCl in diethyl ether was added to precipitate 2-{[6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-amino}-N-methyl-acetamide as a hydrochloride salt. Yield 0.045 gms, M+H=391.

Workup

  1. concentrationconcentrated to an oil under reduced pressure
  2. dissolutionThe oil was dissolved in ethanol
  3. addition1N HCl in diethyl ether was added
  4. customto precipitate 2-{[6-(3-Fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-amino}-N-methyl-acetamide as a hydrochloride salt

Sources & evidence

ORD record
ord-0633ef2d35824bc9bd9fce5e5ab5340c
Source dataset
uspto-grants-2011_07
Patent number
US07981923B2

Reaction notes

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