2-(Methylamino)ethanol → HCID 178484546, compound

HRID 2271555Notes

Reaction equation

HRID 2271555 reaction equation
CS(OC[C@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([Br:24])[CH:22]=3)[N:17]=[CH:16][C:15]=2[C:25]([CH:27]2[CH2:29][CH2:28]2)=[O:26])[CH2:9][CH2:8]1)(=O)=O.[CH3:30][NH:31][CH2:32][CH2:33][OH:34].[CH:35](N(CC)C(C)C)(C)C>C(#N)C.C([O-])(O)=O.[Na+]>[Br:24][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][C:15]([C:25]([CH:27]1[CH2:29][CH2:28]1)=[O:26])=[C:14]2[NH:13][C@H:10]1[CH2:9][CH2:8][C@H:7]([CH2:30][N:31]([CH2:32][CH2:33][OH:34])[CH3:35])[CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 81531DiisopropylethylamineHCID 178505297HCID 178505297, compound

Product 1

HCID 178484546HCID 178484546, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (trans-4-((6-bromo-3-(cyclopropanecarbonyl)quinolin-4-yl)amino)cyclohexyl)methyl methanesulfonate (361 mg, 0.75 mmol) and 2-(methylamino)ethanol (0.30 mL, 3.75 mmol) in acetonitrile (15 mL) was added N,N-diisopropylethylamine (1.0 mL, 5.8 mmol) and the reaction mixture was heated at 70° C. for 16 h. The solution was cooled to room temperature, diluted with a saturated NaHCO3 solution and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated. Purification by column chromatography (silica, 0-20% methanol/dichloromethane) afforded the desired product (150 mg, 43%) as an off-white solid. ESI MS m/z 460 [C23H30BrN3O2+H]+

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customPurification by column chromatography (silica, 0-20% methanol/dichloromethane)

Sources & evidence

ORD record
ord-732289fc3aa94a6ab5fed61e971b736a
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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