Dimethylformamide → HCID 22674164, compound

HRID 1005696Notes

Reaction equation

HRID 1005696 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[Br:12].Cl[C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][N:15]=1.CN(C)C=O.[CH3:29][S-:30].[Na+]>[Cl-].[Na+].O.N1C=CC=CC=1>[Br:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[N:4]=[CH:3][C:2]([NH:1][S:20]([C:17]1[CH:18]=[CH:19][C:14]([S:30][CH3:29])=[N:15][CH:16]=1)(=[O:22])=[O:21])=[CH:11]2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 27927922-Chloro-5-pyridinesulfonyl chlorideHCID 4378561Sodium methanethiolateHCID 226741618-Bromoquinolin-3-amine

Product 1

HCID 22674164HCID 22674164, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

White crystals (197 mg, 0.556 mmol) were obtained in the same manner as in Example 1, except using 100 mg (0.56 mmol) of 3-amino-8-bromoquinoline (Preparation Example 5) and 142 mg (0.67 mmol) of 2-chloro-5-pyridinesulfonyl chloride. To the crystals (60 mg, 0.17 mmol) were added dimethylformamide (1 ml), pyridine (1 ml) and sodium thiomethoxide (111 mg, 1.6 mmol), followed by stirring at room temperature for 3 hours. TO the reaction mixture was added brine, followed by extracting with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated. The resulting residue was purified by silica gel chromatography, to give 62 mg of the title compound.

Workup

  1. extractionby extracting with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f631e972daf34bb6bbcf6e5d0df22fa4
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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