Triethylamine → HCID 57843488, compound

HRID 734968Notes

Reaction equation

HRID 734968 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[N:24]=[CH:23][C:22]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[N:21]3)=[CH:4][N:3]=1.C(N(CC)CC)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43]>ClCCl>[Cl:1][C:2]1[C:7]([NH:8][S:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:10])=[O:11])=[CH:6][C:5]([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[N:24]=[CH:23][C:22]([N:28]2[CH2:29][CH2:30][N:31]([S:42]([CH3:41])(=[O:44])=[O:43])[CH2:32][CH2:33]2)=[N:21]3)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57843339HCID 57843339, compound

Product 1

HCID 57843488HCID 57843488, compoundYield 6.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-{2-chloro-5-[3-(1-piperazinyl)-6-quinoxalinyl]-3-pyridinyl}benzenesulfonamide (0.23 mmol), triethylamine (0.92 mmol), in dichloromethane (5 ml) was added methanesulfonyl chloride (0.25 mmol), which stirred at 50° C. for 18 hours. The reaction was cooled to ambient temperature, concentrated, redissolved in methanol and purified on reverse phase HPLC (0.1% ammonium hydroxide/water in acetonitrile). The desired fractions were combined and concentrated to give the title compound (7.8 mg, 2%) as a white solid. MS(ES)+ m/e 560.2 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. concentrationconcentrated
  3. dissolutionredissolved in methanol
  4. custompurified on reverse phase HPLC (0.1% ammonium hydroxide/water in acetonitrile)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-db825a12eae94b06a0eeaffd34de44de
Source dataset
uspto-grants-2009_09
Patent number
US07592342B2

Reaction notes

Loading…