Dimethylformamide → HCID 22674164, compound

HRID 1173139Notes

Reaction equation

HRID 1173139 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

197 mg (0.556 mmol) of white crystals were obtained using 100 mg (0.56 mmol, Production Example 5b) of 3-amino-8-bromoquinoline and 142 mg (0.67 mmol) of 2-chloro-5-pyridinesulfonyl chloride in the same manner as in Synthetic Example 1b. Dimethylformamide (1 ml), pyridine (1 ml) and 111 mg (1.6 mmol) of sodium thiomethoxide were added to 60 mg (0.17 mmol) of the crystals, followed by stirring at room temperature for 3 hours. Brine was added to the reaction solution, followed by extracting with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated, to give the residue. The 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. customto give the residue
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9cc8a4e4094943219b9ad84b901a812f
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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