Triethylamine → n-[[6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methyl]-2-(4-methylphenylsulfonylamino)acetamide

HRID 2080407Notes

Reaction equation

HRID 2080407 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH:12]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[F:28])[C:13]2[N:18]=[CH:17][C:16]([CH2:19][NH2:20])=[CH:15][CH:14]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.[CH3:48][C:49]1[CH:54]=[CH:53][C:52]([S:55]([NH:58][CH2:59][C:60](O)=[O:61])(=[O:57])=[O:56])=[CH:51][CH:50]=1>CN(C)C1C=CN=CC=1.ClCCl.CCCCCC>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH:12]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[F:28])[C:13]2[N:18]=[CH:17][C:16]([CH2:19][NH:20][C:60](=[O:61])[CH2:59][NH:58][S:55]([C:52]3[CH:53]=[CH:54][C:49]([CH3:48])=[CH:50][CH:51]=3)(=[O:57])=[O:56])=[CH:15][CH:14]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 70653N-((4-Methylphenyl)sulfonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23114616[6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methylamine hydrochloride

Product 1

HCID 23114709n-[[6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methyl]-2-(4-methylphenylsulfonylamino)acetamideYield 73.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

To a dichloromethane (6 ml) solution of the [6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methylamine hydrochloride (40 mg, 0.0898 mmol) obtained in Example 66 were added triethylamine (45 μl, 0.324 mmol), 4-dimethylaminopyridine (5 mg, 0.0449 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (21 mg, 0.108 mmol) and N-p-tosylglycine (25 mg, 0.108 mmol). The resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with dichloromethane. The diluted mixture was then washed sequentially with water, a saturated aqueous solution of sodium bicarbonate and brine. The organic layer thus obtained was dried over magnesium sulfate and then, concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=2.3 eluate was concentrated under reduced pressure to give the title compound (41 mg, 0.0661 mmol, 73%) as a white powder.

Workup

  1. washThe diluted mixture was then washed sequentially with water
  2. customThe organic layer thus obtained
  3. dry with materialwas dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. concentrationethyl acetate=2.3 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-abd71662f470433c84af16f536aef098
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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