Triethylamine → HCID 18348968, compound

HRID 2268664Notes

Reaction equation

HRID 2268664 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH:32]([CH3:34])[CH3:33])[C:13](=[O:31])[C:14]1[CH:19]=[C:18]([O:20][CH2:21][CH2:22][NH:23][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[CH:17]=[C:16]([Cl:30])[CH:15]=1.[CH3:35][S:36](Cl)(=[O:38])=[O:37].C(N(CC)CC)C>C(#N)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:30][C:16]1[CH:15]=[C:14]([CH:19]=[C:18]([O:20][CH2:21][CH2:22][NH:23][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[CH:17]=1)[C:13]([N:12]([CH:32]([CH3:34])[CH3:33])[CH2:11][CH2:10][CH2:9][NH:8][S:36]([CH3:35])(=[O:38])=[O:37])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18349209HCID 18349209, compound

Product 1

HCID 18348968HCID 18348968, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of N-(3-amino-propyl)-3-chloro-N-isopropyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzamide trifluoroacetate (0.02 g) in dry acetonitrile (1 ml) was added a mixture of methanesulfonyl chloride (0.005 g) and triethylamine (0.017 ml) in acetonitrile (1 ml). The resultant mixture was stirred at room temperature for 15 h, and then concentrated under reduced pressure. The residue was stored in a mixture of dichloromethane (1 ml) and trifluoroacetic acid (2 ml) for 4 h, and then concentrated under reduced pressure. The residue was then subjected to preparative hplc and the title compound obtained as a colourless oil by concentration of the required fraction under reduced pressure and drying by repetitive addition of acetonitrile and concentration under reduced pressure.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was stored in a mixture of dichloromethane (1 ml) and trifluoroacetic acid (2 ml) for 4 h
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cc2932d8e9814cbfa96bb26158c498bf
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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