Triethylamine → HCID 28376252, compound

HRID 2366064Notes

Reaction equation

HRID 2366064 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.C(N(CC)CC)C.[Cl:16][C:17]1[N:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>C(Cl)Cl>[Cl:16][C:17]1[N:22]=[CH:21][C:20]([S:23]([N:2]([CH3:1])[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 207272-Pyridinamine, N-methyl-HCID 27927922-Chloro-5-pyridinesulfonyl chloride

Product 1

HCID 28376252HCID 28376252, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.3 g (11.8 mmol) of N-methylpyridin-2-amine in 25 mL of DCM are added, at 0° C., 3.3 mL (23.6 mmol) of triethylamine and then, portionwise, 2.5 g (11.8 mmol) of 6-chloropyridine-3-sulfonyl chloride (prepared according to document WO 98/40332). After stirring for 12 hours at room temperature, the reaction medium is taken up in 100 mL of DCM, washed successively with 100 mL of water and 30 mL of brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, eluting with a 4/1 cyclohexane/EtOAc mixture. After concentrating under reduced pressure, 2.8 g of 6-chloro-N-methyl-N-pyridin-2-ylpyridine-3-sulfonamide are obtained in the form of a brown solid.

Workup

  1. washwashed successively with 100 mL of water and 30 mL of brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica gel
  7. washeluting with a 4/1 cyclohexane/EtOAc mixture
  8. concentrationAfter concentrating under reduced pressure, 2.8 g of 6-chloro-N-methyl-N-pyridin-2-ylpyridine-3-sulfonamide
  9. customare obtained in the form of a brown solid

Sources & evidence

ORD record
ord-6f3f7d7840674db9ac0c229cd80a9ca7
Source dataset
uspto-grants-2014_04
Patent number
US08697731B2

Reaction notes

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