2-Bromoethyl methyl ether → HCID 118323999, compound

HRID 1778273Notes

Reaction equation

HRID 1778273 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=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][N:24]([S:27]([C:30]([F:33])([F:32])[F:31])(=[O:29])=[O:28])[CH2:23][CH2:22]2)=[CH:4][CH:3]=1.Br[CH2:42][CH2:43][O:44][CH3:45]>CC#N.CCOC(C)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:34]2[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[C:14]([O:19][CH2:42][CH2:43][O:44][CH3:45])[CH:13]=[C:12]3[NH:20][CH:21]2[CH2:26][CH2:25][N:24]([S:27]([C:30]([F:33])([F:31])[F:32])(=[O:29])=[O:28])[CH2:23][CH2:22]2)=[CH:4][CH:3]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:34]2[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH2:42][CH2:43][O:44][CH3:45])[C:14](=[O:19])[CH:13]=[C:12]3[NH:20][CH:21]2[CH2:26][CH2:25][N:24]([S:27]([C:30]([F:33])([F:31])[F:32])(=[O:29])=[O:28])[CH2:23][CH2:22]2)=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 809722-Bromoethyl methyl ether2×HCID 91844670HCID 91844670, compound

Product 2

HCID 118323999HCID 118323999, compoundYield 80%HCID 118324131HCID 118324131, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 6-(bis(4-chlorophenyl)methyl)-4-((1-((trifluoromethyl)sulfonyl)piperidin-4-yl)amino)quinolin-2(1H)-one (66.7 mg, 0.109 mmol), and 1-bromo-2-methoxyethane (0.0123 mL, 0.131 mmol) in CH3CN (2 mL) was heated at 75° C. overnight. Additional 1-bromo-2-methoxyethane (0.006 mL) was added and the reaction mixture stirred for another 24 h. The reaction mixture was diluted with EtOAc and water. The aqueous layer was extracted with EtOAc twice. The combined organics were concentrated and purified by silica column (25% EtOAc/hexanes) to yield 6-(bis(4-chlorophenyl)methyl)-2-(2-methoxyethoxy)-N-(1-((trifluoromethyl)sulfonyl)piperidin-4-yl)quinolin-4-amine and (80% EtOAc/hexanes) 6-(bis(4-chlorophenyl)methyl)-1-(2-methoxyethyl)-4-((1-((trifluoromethyl)sulfonyl)piperidin-4-yl)amino)quinolin-2(1H)-one.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc twice
  2. concentrationThe combined organics were concentrated
  3. custompurified by silica column (25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-204def0cb0234721a2a7a5a6e4d378bc
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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