Water → Propane-2-sulfonic acid [5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide

HRID 1774803Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[C:14](=[O:20])[CH2:13][CH2:12]3)[CH:6]=[N:7][CH:8]=1.C(N(CC)CC)C.[CH:28]([S:31](Cl)(=[O:33])=[O:32])([CH3:30])[CH3:29].O>C(Cl)Cl>[CH3:19][N:15]1[C:16]2[C:11](=[CH:10][C:9]([C:5]3[CH:4]=[C:3]([CH2:2][NH:1][S:31]([CH:28]([CH3:30])[CH3:29])(=[O:33])=[O:32])[CH:8]=[N:7][CH:6]=3)=[CH:18][CH:17]=2)[CH2:12][CH2:13][C:14]1=[O:20]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-(5-aminomethyl-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-quinolin-2-one (example 36, 0.05 g, 0.187 mmol) in DCM (1 mL) cooled to 0° C. were added triethylamine (0.038 g, 0.374 mmol) and isopropylsulfonylchloride (0.029 g, 0.206 mmol). The resulting suspension was stirred at 0° C. for 4 h and then allowed to warm up to room temperature and stirring was continued for 2 h. The reaction mixture was diluted with DCM, poured into H2O (5 mL) and extracted with DCM (2×10 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(1% NH4OH)-DCM gradient to give the title compound (0.023 g, 33%) as a white foam. MS: 374.1 (M+H+).

Workup

temperatureto warm up to room temperature
stirringstirring
waitwas continued for 2 h
extractionextracted with DCM (2×10 mL)
dry with materialCombined organics were dried over Na2SO4
filtrationfiltered
customevaporated to dryness
customThe residue was purified by silica gel flash chromatography
washeluting with a 0 to 10% MeOH(1% NH4OH)-DCM gradient

Sources & evidence

ORD record: ord-59529ce4e6584e93a9ba5a73d4bfd18a
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260408B2

Reaction notes

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