Acetyl chloride → N-{6-[3-(4-tert-Butyl-benzenesulfonylamino)-5-chloro-pyridine-2-carbonyl]-pyridin-2-yl}-acetamide

HRID 419216Notes

Reaction equation

HRID 419216 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([C:10]2[C:15]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=3)(=[O:19])=[O:18])=[CH:14][C:13]([Cl:30])=[CH:12][N:11]=2)=[O:9])[CH:5]=[CH:4][CH:3]=1.[C:31](Cl)(=[O:33])[CH3:32]>N1C=CC=CC=1.O1CCOCC1>[C:26]([C:23]1[CH:22]=[CH:21][C:20]([S:17]([NH:16][C:15]2[C:10]([C:8]([C:6]3[N:7]=[C:2]([NH:1][C:31](=[O:33])[CH3:32])[CH:3]=[CH:4][CH:5]=3)=[O:9])=[N:11][CH:12]=[C:13]([Cl:30])[CH:14]=2)(=[O:18])=[O:19])=[CH:25][CH:24]=1)([CH3:27])([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 57942125N-[2-(6-amino-pyridine-2-carbonyl)-5-chloro-pyridin-3-yl]-4-tert-butyl-benzenesulfonamide

Product 1

HCID 57942181N-{6-[3-(4-tert-Butyl-benzenesulfonylamino)-5-chloro-pyridine-2-carbonyl]-pyridin-2-yl}-acetamide

Reagents, catalysts & solvents 1

HCID 22147851Pyridine dioxaneSolvent

Conditions

Temperature
60 °C

Procedure

N-[2-(6-amino-pyridine-2-carbonyl)-5-chloro-pyridin-3-yl]-4-tert-butyl-benzenesulfonamide (52 mg, 0.1 mmol) in pyridine/1,4-dioxane (1:1, 4 mL) was treated with acetyl chloride (100 mg) and then stirred at 60° C. for 2 h. After evaporation of solvent under reduced pressure, to the mixture was added THF (5 mL), followed by NaOH (2 N, 2 mL) and stirred at room temperature for another 2 h. The mixture was diluted with EtOAc and the organics were washed with 1 N HCl, NaHCO3 (saturated), and brine; dried over MgSO4, concentrated under reduced pressure, and purified through automated normal-phase chromatography to afford the title compound: 1H NMR (400 MHz, CDCl3) δ 10.80 (s, 1H), 8.37 (d, 1H), 8.22 (m, 2 H), 8.14 (s, 1H), 7.80 (m, 3H), 7.46 (m, 3H), 2.20 (s, 3H), 1.23 (s, 9H); MS (ES) (M+H)+ expected 487.1, found 487.1.

Workup

  1. customAfter evaporation of solvent under reduced pressure
  2. additionto the mixture was added THF (5 mL)
  3. stirringstirred at room temperature for another 2 h
  4. additionThe mixture was diluted with EtOAc
  5. washthe organics were washed with 1 N HCl, NaHCO3 (saturated), and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. custompurified

Sources & evidence

ORD record
ord-258f62844eed4911a5ee2a322062ef90
Source dataset
uspto-grants-2012_01
Patent number
US08093247B2

Reaction notes

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