Hydrochloric Acid → HCID 178467065, compound

HRID 2271546Notes

Reaction equation

HRID 2271546 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([C:13](=[O:15])[CH3:14])=[C:6]2Cl.C([O-])([O-])=O.[K+].[K+].[CH:23]([N:26]([CH2:30][CH3:31])[CH:27](C)C)(C)C>O1CCOCC1.CN(C=O)C>[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([C:13](=[O:15])[CH3:14])=[C:6]2[NH:9][C@H:10]1[CH2:11][CH2:12][C@H:3]([CH2:31][CH2:30][N:26]([CH3:23])[CH3:27])[CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 667154831-(6-Bromo-4-chloroquinolin-3-YL)ethanone

Product 1

HCID 178467065HCID 178467065, compoundYield 108.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

Following general procedure A-1, tert-butyl (trans-4-(2-(dimethylamino)ethyl)cyclohexyl) carbamate (336 mg, 1.24 mmol) was reacted with 6 N aqueous HCl (2 mL) to afford a viscous colorless oil. The oil was dissolved in dioxane (10 mL) and DMF (5 mL) followed by the addition of 1-(6-bromo-4-chloroquinolin-3-yl)ethanone (285 mg, 1.0 mmol), K2CO3 (0.55 g, 4.0 mmol), and N,N-diisopropylethylamine (1.0 mL, 5.8 mmol) and the resultant suspension was heated at 100° C. for 16 h. The reaction mixture 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 and concentrated. Purification by column chromatography (silica, 0-20% methanol/dichloromethane) afforded the desired product (227 mg, 54%) as a light yellow-brown solid. ESI MS m/z 418 [C21H28BrN3O+H]+

Workup

  1. customto afford a viscous colorless oil
  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-1eae9ca583734ee1836f531338894d19
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

Loading…