2-Chloro-5-pyridinesulfonyl chloride → (S)-6-chloro-N-(1,1,1-trifluoropropan-2-yl)pyridine-3-sulfonamide

HRID 1027999Notes

Reaction equation

HRID 1027999 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][C:14]([F:19])([F:18])[C@@H:15]([NH2:17])[CH3:16]>N1C=CC=CC=1.C(OCC)(=O)C>[F:13][C:14]([F:19])([F:18])[C@@H:15]([NH:17][S:8]([C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[CH:7][CH:6]=1)(=[O:10])=[O:9])[CH3:16]

Participants

5

Reactant 2

HCID 27927922-Chloro-5-pyridinesulfonyl chlorideHCID 130939192-Propanamine, 1,1,1-trifluoro-, hydrochloride (1:1), (2S)-

Product 1

HCID 86665920(S)-6-chloro-N-(1,1,1-trifluoropropan-2-yl)pyridine-3-sulfonamideYield 80.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-chloropyridine-5-sulfonyl chloride (12 g, 56.6 mmol) was added to a solution of (S)-1,1,1-trifluoropropan-2-amine hydrochloride (7.8 g, 51.2 mmol) in pyridine (15 mL) at 0° C. The mixture was stirred at room temperature for 10 minutes and diluted with ethyl acetate (200 ml) and washed with 3 N aq. HCl (2×100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. The solid was triturated with hexane (2×40 mL) and filtered to provide (S)-6-chloro-pyridine-3-sulfonic acid (2,2,2-trifluoro-1-methyl-ethyl)-amide as an off-white solid (11.84 g, 75%). 1H NMR (500 MHz, CDCl3): δ0.81 (1H, d, J=2.4 Hz), 8.18 (1H, dd, J=2.5 Hz, 2.6 Hz), 7.51 (1H, d, J=8.8 Hz), 4.92 (1H, br s), 4.08 (1H, m), 1.45 (3H, d, J=7.0 Hz).

Workup

  1. washwashed with 3 N aq. HCl (2×100 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe solid was triturated with hexane (2×40 mL)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-396d02eceeb248d0a4fcaabaace97a19
Source dataset
uspto-grants-2014_05
Patent number
US08735414B2

Reaction notes

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