3-Chloro-2-methylbenzenesulfonyl chloride → HCID 68842273, compound

HRID 1454913Notes

Reaction equation

HRID 1454913 reaction equation
[N:1]1([C:7]2[CH:8]=[N:9][C:10]([NH2:13])=[CH:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:14][C:15]1[C:16]([CH3:25])=[C:17]([S:21](Cl)(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1>N1C=CC=CC=1>[Cl:14][C:15]1[C:16]([CH3:25])=[C:17]([S:21]([NH:13][C:10]2[N:9]=[CH:8][C:7]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[CH:12][CH:11]=2)(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 5227343-Chloro-2-methylbenzenesulfonyl chlorideHCID 112982775-(Piperidin-1-yl)pyridin-2-amine

Product 1

HCID 68842273HCID 68842273, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

3,4,5,6-Tetrahydro-2H-[1,3′]bipyridinyl-6′-ylamine (0.19 g) and 3-chloro-2-methylbenzenesulfonyl chloride (0.24 g) were dissolved in pyridine (4 mL) and heated at 50° C. over night. The mixture was concentrated in vacuo, taken up in ethyl acetate and extracted with 1M Cu(II)SO4 solution. The organic layer was washed once again with Cu(II)SO4 solution, dried over Na2SO4 and evaporated in vacuo. The product was purified by flash chromatography on silica gel (gradient of ethyl acetate in heptane) to give 3-chloro-2-methyl-N-(3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-6′-yl)-benzenesulfonamide (0.1 g) as a light brown foam. MS (ESI−): 364.0 ([M−H]−).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with 1M Cu(II)SO4 solution
  3. washThe organic layer was washed once again with Cu(II)SO4 solution
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo
  6. customThe product was purified by flash chromatography on silica gel (gradient of ethyl acetate in heptane)

Sources & evidence

ORD record
ord-96ec01bdd7bb4cb897db8fde3936798f
Source dataset
uspto-grants-2009_01
Patent number
US07482341B2

Reaction notes

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