Triethylamine → HCID 53774435, compound

HRID 2288185Notes

Reaction equation

HRID 2288185 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]([F:41])([F:40])[C:8]1[CH:9]=[C:10]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][OH:22])[CH2:15][C@H:14]1[CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1)=[O:12].C(N(CC)CC)C>ClCCl>[F:41][C:7]([F:6])([F:40])[C:8]1[CH:9]=[C:10]([CH:33]=[C:34]([C:36]([F:37])([F:38])[F:39])[CH:35]=1)[C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][O:22][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:15][C@H:14]1[CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1)=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54127973HCID 54127973, compound

Product 1

HCID 53774435HCID 53774435, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of methanesulfonyl chloride (1.1 g) in dichloromethane (4 ml) was added to a stirred solution of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-(3-hydroxypropyl)-2-(1H-indol-3-ylmethyl)piperazine (4.99 g) and triethylamine (1.1 g) in dichloromethane (50 ml) at ice-bath temperature over a 20-minute period. After being stirred at the same temperature for 1 hour, the reaction mixture was diluted with dichloromethane (50 ml) and then washed with water and aqueous sodium bicarbonate solution. The dichloromethane layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using dichloromethane-methanol (30:1) as an eluent to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-4-(3-methylsulfonyloxypropyl)piperazine (4.31 g) as a powder.

Workup

  1. washwashed with water and aqueous sodium bicarbonate solution
  2. dry with materialThe dichloromethane layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-74dc4eee995643de82e20c129842fa79
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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