Pyridine → HCID 118324077, compound

HRID 1778316Notes

Reaction equation

HRID 1778316 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH:13]=[C:12]3[NH:20][CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.C1COCC1.Cl[S:46]([CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])(=[O:48])=[O:47]>ClCCl>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14](=[O:19])[CH:13]=[C:12]3[NH:20][CH:21]2[CH2:22][CH2:23][N:24]([S:46]([CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])(=[O:48])=[O:47])[CH2:25][CH2:26]2)=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 12225100Ethyl (chlorosulfonyl)acetateHCID 118323976HCID 118323976, compound

Product 1

HCID 118324077HCID 118324077, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 25-mL one-neck round bottom flask with stir bar was added 6-(bis(4-chlorophenyl)methyl)-4-(piperidin-4-ylamino)quinolin-2(1H)-one (0.1 g, 0.209 mmol), pyridine (0.02 mL; 0.247 mmol) and THF (3 mL) at 0° C. To the resulting solution was added a solution of ethyl 2-(chlorosulfonyl)acetate (43 mg; 0.23 mmol) in dichloromethane (1 mL) over 10 min. The reaction was then warmed to room temperature. The reaction was quenched with 1N HCl (10 mL) and DCM (10 mL). The aqueous layer was extracted with DCM and the organics were concentrated. The resulting residue was purified by silica gel column chromatography (0-10% MeOH/DCM) to yield ethyl 2-((4-((6-(bis(4-chlorophenyl)methyl)-2-oxo-1,2-dihydroquinolin-4-yl)amino)piperidin-1-yl)sulfonyl)acetate as an orange oil.

Workup

  1. customThe reaction was quenched with 1N HCl (10 mL) and DCM (10 mL)
  2. extractionThe aqueous layer was extracted with DCM
  3. concentrationthe organics were concentrated
  4. customThe resulting residue was purified by silica gel column chromatography (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-26f5b7512d6649f5b24129c32b75fbba
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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