Water → HCID 71533145, compound

HRID 1774783Notes

Reaction equation

HRID 1774783 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13](=[O:19])[CH2:12][CH2:11]3)[CH:5]=[N:6][CH:7]=1.C(N(CC)CC)C.[CH2:27]([S:29](Cl)(=[O:31])=[O:30])[CH3:28].O>C(Cl)Cl>[CH3:18][N:14]1[C:15]2[C:10](=[CH:9][C:8]([C:4]3[CH:3]=[C:2]([NH:1][S:29]([CH2:27][CH3:28])(=[O:31])=[O:30])[CH:7]=[N:6][CH:5]=3)=[CH:17][CH:16]=2)[CH2:11][CH2:12][C:13]1=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 86679106HCID 86679106, compound

Product 1

HCID 71533145HCID 71533145, compoundYield 25.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-(5-amino-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-quinolin-2-one (intermediate A-2, 0.02 g, 0.079 mmol) in DCM (0.5 mL) was added triethylamine (0.024 g, 0.237 mmol) followed by ethanesulfonyl chloride (0.01 g, 0.079 mmol) and the reaction mixture was stirred at room temperature for 1 h. The mixture was diluted with DCM, poured into water (5 mL) and the aqueous layer was extracted with DCM (2×20 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 10% MeOH-DCM gradient to give the title compound (0.007 g, 23%) as a brown solid. MS: 346.0 (M+H+).

Workup

  1. extractionthe aqueous layer was extracted with DCM (2×20 mL)
  2. dry with materialCombined organics were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified by silica gel flash chromatography
  6. washeluting with a 0 to 10% MeOH-DCM gradient

Sources & evidence

ORD record
ord-1d8909c7e7484016815ea55d144e1cc5
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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