Potassium Carbonate → HCID 178493186, compound

HRID 2271553Notes

Reaction equation

HRID 2271553 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.Cl.[CH3:31][O:32][CH:33]1[CH2:37][CH2:36][NH:35][CH2:34]1.C([O-])([O-])=O.[K+].[K+].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:35]2[CH2:36][CH2:37][CH:33]([O:32][CH3:31])[CH2:34]2)[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 220176303-Methoxypyrrolidine hydrochlorideHCID 178505297HCID 178505297, compound

Product 1

HCID 178493186HCID 178493186, compoundYield 42.5%

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-methoxypyrrolidine hydrochloride (410 mg, 2.98 mmol) in acetonitrile (15 mL) was added K2CO3 (1.24 g, 9 mmol) and KI (300 mg, 1.81 mmol) and N,N-diisopropylethylamine (0.5 mL, 2.9 mmol) and the reaction mixture was heated at 50° C. for 16 h and 80° C. for 24 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 purification by column chromatography (silica, 0-20% methanol/dichloromethane) to afford the desired product (155 mg, 42%) as an off-white solid. ESI MS m/z 486 [C25H32BrN3O2+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. custompurification by column chromatography (silica, 0-20% methanol/dichloromethane)

Sources & evidence

ORD record
ord-41b5972ae61d42e0af5307975bd15ae3
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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