Diisopropylethylamine → HCID 178519794, compound

HRID 2271554Notes

Reaction equation

HRID 2271554 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]([CH:27]2[CH2:29][CH2:28]2)=[O:26])[CH2:9][CH2:8]1)(=O)=O.[OH:30][CH:31]1[CH2:35][CH2:34][NH:33][CH2:32]1.C(N(CC)C(C)C)(C)C>C(#N)C>[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[CH2:28][CH2:29]1)=[O:26])=[C:14]2[NH:13][C@H:10]1[CH2:9][CH2:8][C@H:7]([CH2:6][N:33]2[CH2:34][CH2:35][CH:31]([OH:30])[CH2:32]2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 982104-HydroxypyrrolidineHCID 178505297HCID 178505297, compound

Product 1

HCID 178519794HCID 178519794, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (trans-4-((6-bromo-3-(cyclopropanecarbonyl)quinolin-4-yl)amino)cyclohexyl)methyl methanesulfonate (362 mg, 0.75 mmol) and 3-hydroxypyrrolidine (262 mg, 3.0 mmol) in acetonitrile (15 mL) was added N,N-diisopropylethylamine (1.0 mL, 5.8 mmol) and the reaction mixture was heated at 80° C. for 16 h. The solution was cooled to room temperature, diluted 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 (174 mg, 49%) as an off-white solid. ESI MS m/z 472 [C24H30BrN3O2+H]+

Workup

  1. temperatureThe solution was cooled to room temperature
  2. additiondiluted
  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-ee8e4125aa48429c8e37a5ac56588cb8
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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