Pyridine → HCID 21224898, compound

HRID 1584662Notes

Reaction equation

HRID 1584662 reaction equation
[C:1]1([C:7]2[NH:8][C:9](=[O:33])[N:10]([S:12]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([C:24](=[O:32])[C:25]3[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=3)[CH2:19][CH2:18]4)(=[O:14])=[O:13])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[Cl:40][CH2:41][C:42](Cl)=[O:43]>ClCCl>[C:1]1([C:7]2[NH:8][C:9](=[O:33])[N:10]([S:12]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([C:24](=[O:32])[C:25]3[CH:26]=[CH:27][C:28]([NH:31][C:42](=[O:43])[CH2:41][Cl:40])=[CH:29][CH:30]=3)[CH2:19][CH2:18]4)(=[O:13])=[O:14])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 21224906HCID 21224906, compound

Product 1

HCID 21224898HCID 21224898, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Phenyl-1-[N-(4-aminobenzoyl)indoline-5-sulfonyl]-2-imidazolone (150 mg, 0.3 mmol) prepared in Example 10 was dissolved in 10 ml of dichloromethane. Pyridine (73 μl, 0.9 mmol) and chloroacetylchloride (36 μl, 0.45 mmol) were added thereto one after another, and then the reaction mixture was stirred at room temperature under nitrogen atmosphere for 2 hours. After stirring, the reaction mixture was diluted with 30 ml of dichloromethane, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent:dichloromethane/methanol=10/1, v/v) to afford 130 mg of the title compound as a white solid.

Workup

  1. stirringAfter stirring
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-79b38f7682fb430f91193bf6e41b710c
Source dataset
uspto-grants-1999_08
Patent number
US05932742

Reaction notes

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