Benzenesulfonamide → HCID 15491312, compound

HRID 895344Notes

Reaction equation

HRID 895344 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][O:7][CH2:8][CH:9]([N:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][O:24][CH2:25][C:26]([OH:28])=O)[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:38]1([S:44]([NH2:47])(=[O:46])=[O:45])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:31]=1)[CH2:6][O:7][CH2:8][CH:9]([N:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][O:24][CH2:25][C:26]([NH:47][S:44]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)(=[O:46])=[O:45])=[O:28])[CH2:18][CH2:17]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 7370BenzenesulfonamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 10230370HCID 10230370, compound2×

Product 1

HCID 15491312HCID 15491312, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a round-bottomed flask fitted with a reflux condenser and a thermometer was introduced (2-{4-[2-(3,5-Bis-trifluoromethyl-benzyloxy)-1-phenyl-ethyl]-piperazin-1-yl}-ethoxy)-acetic acid (compound 235 prepared at example 1.4.2; 2.7 g, 4.54 mmoles) dissolved in CH2Cl2 (25 ml). Benzenesulphonamide (1.07 g, 6.8 mmoles), DMAP (10 mg, 0.45 mmoles) and EDCI (0.96 g, 5 mmoles) were added to the solution and the reaction mixture was stirred at room temperature for 48 hours. The organic solution was washed with HCl 0.1N and brine, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel (eluent: CH2Cl2/MeOH/NH3: 95/5/0.2 v/v/v) to afford the monohydrate of N-[(2-{4-[2-(3,5-Bis-trifluoromethyl-benzyloxy)-1-phenyl-ethyl]-piperazin-1-yl}-ethoxy)-acetyl]-benzenesulfonamide (compound 306; 1.5 g, 50%) as a beige solid.

Workup

  1. customIn a round-bottomed flask fitted with a reflux condenser
  2. washThe organic solution was washed with HCl 0.1N and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel (eluent: CH2Cl2/MeOH/NH3: 95/5/0.2 v/v/v)

Sources & evidence

ORD record
ord-db1cd4c291c74ba3ab60ff6748a4a4a9
Source dataset
uspto-grants-2005_07
Patent number
US06916797B2

Reaction notes

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