4-Chlorobenzenesulfonyl chloride → HCID 17838655, compound

HRID 1173141Notes

Reaction equation

HRID 1173141 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[N:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:1][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[N:7][CH:8]=3)[N:3]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5893531,6-Naphthyridin-2-amine

Product 1

HCID 17838655HCID 17838655, compoundYield 21.44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

2-Amino-1,6-naphthyridine (200 mg, Production Example 25b) was dissolved in dichloromethane (6.0 ml), to which were then added triethylamine (0.20 ml) and 4-chlorobenzenesulfonyl chloride (0.31 g), followed by stirring at 40° C. for 1.5 hours. An aqueous saturated sodium bicarbonate was added thereto, followed by extracting with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column, to give the title compound (84 mg, 21.44%) as pale yellow crystals.

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column

Sources & evidence

ORD record
ord-ebe0bf55649d45c29fab50e142a0014b
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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