2-Chloro-5-pyridinesulfonyl chloride → HCID 86668140, compound

HRID 1027985Notes

Reaction equation

HRID 1027985 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][N:3]=1.Cl.[F:13][CH2:14][CH:15]([NH2:18])[CH2:16][F:17]>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([S:8]([NH:18][CH:15]([CH2:16][F:17])[CH2:14][F:13])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 27927922-Chloro-5-pyridinesulfonyl chlorideHCID 231177571,3-Difluoropropan-2-amine--hydrogen chloride (1/1)

Product 1

HCID 86668140HCID 86668140, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloropyridine-5-sulfonyl chloride (18 g, 85 mmol) was added to a solution of 1,3-difluoro-2-propylamine hydrochloride (11.2 g, 58.1 mmol) in pyridine (25 mL) at 0° C. The reaction mixture was stirred at room temperature for 30 minutes, diluted with ethyl acetate (200 mL) and washed with 3N aq. HCl (3×100 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The residue was triturated with hexane (2×50 mL) and filtered to provide the title compound as an off-white solid (15.7 g, 70%). 1H NMR (500 MHz, CDCl3): δ 8.79 (1H, d, J=2.4 Hz), 8.17 (1H, dd, J=2.6 Hz, 2.5 Hz), 7.49 (1H, d, J=8.2 Hz), 5.25 (1H br s), 4.58 (2H, m), 4.47 (2H, m), 3.77 (1H, m).

Workup

  1. washwashed with 3N aq. HCl (3×100 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was triturated with hexane (2×50 mL)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-84caa07c0d7e4b6f84fc74ed8ee78c4e
Source dataset
uspto-grants-2014_05
Patent number
US08735414B2

Reaction notes

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