Diisopropylethylamine → HCID 178467067, compound

HRID 2271547Notes

Reaction equation

HRID 2271547 reaction equation
CS(O[CH2:6][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](=[O:27])[CH3:26])[CH2:9][CH2:8]1)(=O)=O.[N:28]1([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(N(CC)C(C)C)(C)C>C(#N)C.O1CCOCC1>[C:25]([C:15]1[CH:16]=[N:17][C:18]2[C:23]([C:14]=1[NH:13][C@H:10]1[CH2:11][CH2:12][C@H:7]([CH2:6][N:31]3[CH2:32][CH2:33][N:28]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:29][CH2:30]3)[CH2:8][CH2:9]1)=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=2)(=[O:27])[CH3:26]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 178467069HCID 178467069, compound

Product 1

HCID 178467067HCID 178467067, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of ((trans-4-((3-acetyl-6-bromoquinolin-4-yl)amino)cyclohexyl)methyl methanesulfonate (300 mg, 0.66 mmol) and tert-butyl piperazine-1-carboxylate (566 mg, 3.0 mmol) in acetonitrile (5 mL) and dioxane (5 mL) was added KI (500 mg, 3.0 mmol) and N,N-diisopropylethylamine (0.60 mL, 3.44 mmol) and the reaction mixture was heated at 70° C. for 16 h. The solution was cooled to room temperature, diluted with satd. aq. NaHCO3 and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (silica, 0-20% methanol/dichloromethane) to afford the desired product (248 mg, 69%) as an off-white solid. ESI MS m/z 545 [C27H37BrN4O3+H]+

Workup

  1. temperatureThe solution was cooled to room temperature
  2. additiondiluted with satd
  3. extractionaq. NaHCO3 and extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurified by column chromatography (silica, 0-20% methanol/dichloromethane)

Sources & evidence

ORD record
ord-c3f7874f7d254f24b40a5f13af7077d3
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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