Pyridine → HCID 71506383, compound

HRID 929354Notes

Reaction equation

HRID 929354 reaction equation
[NH2:1][C:2]1[C:3]([F:23])=[C:4]([C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][C:16]([Cl:22])=[N:15]3)=[O:11])[C:5]([F:9])=[C:6]([F:8])[CH:7]=1.[CH2:24]([S:27](Cl)(=[O:29])=[O:28])[CH2:25][CH3:26].N1C=CC=CC=1>C(Cl)Cl>[Cl:22][C:16]1[CH:17]=[N:18][C:19]2[C:14]([N:15]=1)=[CH:13][C:12]([C:10]([C:4]1[C:3]([F:23])=[C:2]([NH:1][S:27]([CH2:24][CH2:25][CH3:26])(=[O:29])=[O:28])[CH:7]=[C:6]([F:8])[C:5]=1[F:9])=[O:11])=[CH:21][CH:20]=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 662791-Propanesulfonyl chlorideHCID 86677178HCID 86677178, compound

Product 1

HCID 71506383HCID 71506383, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-amino-2,5,6-trifluorophenyl)(3-chloroquinoxalin-6-yl)methanone (40 mg, 0.119 mmol, 1.0 eq.) in DCM (5 mL) was added propane-1-sulfonyl chloride (84.6 mg, 0.593 mmol, 5.0 eq.) and pyridine (94 mg, 1.19 mmol, 10.0 eq.). The mixture was heated under reflux overnight, then concentrated. The resulting residue was purified by flash column chromatography (PE/EA=4/1, v/v) and Prep-TLC to afford N-(3-(3-chloroquinoxaline-6-carbonyl)-2,4,5-trifluorophenyl)propane-1-sulfonamide (8 mg, 15.2%). LRMS (M−H−) m/z calculated 442.0, found 442.0. 1H NMR (CDCl3, 400 MHz) δ 8.91 (s, 1 H), 8.27-8.41 (m, 3 H), 7.71-7.77 (m, 1 H), 6.63 (s, 1 H), 3.13-3.17 (t, 2 H), 1.86-1.94 (q, 2 H), 1.07-1.11 (t, 3 H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationconcentrated
  4. customThe resulting residue was purified by flash column chromatography (PE/EA=4/1

Sources & evidence

ORD record
ord-0cff7b16d09e40c0b5bc6ba3b11a09f0
Source dataset
uspto-grants-2016_03
Patent number
US09295671B2

Reaction notes

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