Triethylamine → HCID 22103724, compound

HRID 1457200Notes

Reaction equation

HRID 1457200 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][N:14]=2)[CH:7]=[CH:6][C:5]=1[C:15]1[C:16]([S:21]([NH:24][C:25]2[O:29][N:28]=[C:27]([CH3:30])[C:26]=2[CH3:31])(=[O:23])=[O:22])=[CH:17][CH:18]=[CH:19][CH:20]=1.[Cl:32][C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35](Cl)=[O:36].C(N(CC)CC)C>C(Cl)Cl>[Cl:32][C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35]([N:2]([CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][N:14]=2)[CH:7]=[CH:6][C:5]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([NH:24][C:25]1[O:29][N:28]=[C:27]([CH3:30])[C:26]=1[CH3:31])(=[O:22])=[O:23])[CH3:1])=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 691102-Chlorobenzoyl chlorideHCID 22103549HCID 22103549, compound

Product 1

HCID 22103724HCID 22103724, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.12 g (0.29 mmol) of 2'-[(methylamino)methyl]-N-(3,4-dimethyl-5-isoxazolyl)-4'-(2-oxazolyl)[1,1'-biphenyl]-2-sulfonamide (prepared as described in Step (A) of Example 28) in 5 mL of CH2Cl2, 0.061 g (0.348 mmol) of 2-chlorobenzoyl chloride and 0.065 g (0.638 mmol) of triethylamine were added. The mixture was then stirred at room temperature for 12 hr and evaporated. The residue was purified by reverse phase preparative HPLC on a 30×500 mm ODS S10 column using 72% solvent B (90% MeOH, 10% H2O, 0.1% TFA) and 28% solvent A (10% MeOH, 90% H2O, 0.1% TFA). The appropriate fractions were collected and neutralized with aqueous sodium bicarbonate to pH 7 and concentrated to 10 mL. The solution was then acidified to pH 4 using aqueous sodium bisulfate and the white solid was filtered and dried to provide 0.043 g (26%) of the title compound of this Example as a white solid.

Workup

  1. customevaporated
  2. customThe residue was purified by reverse phase preparative HPLC on a 30×500 mm ODS S10 column
  3. customThe appropriate fractions were collected
  4. concentrationconcentrated to 10 mL
  5. filtrationthe white solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-728b4ff72c4a441ab5aa9a1254bba33f
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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