Nitrogen → HCID 67970839, compound

HRID 882073Notes

Reaction equation

HRID 882073 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH3:23])[C:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:11](=[O:22])[C:10]=3[C:5]2=[CH:4][CH:3]=1.[CH2:24]([O:31][C:32]1[CH:37]=[CH:36][NH:35][C:34](=[O:38])[CH:33]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+].N#N.CN[C@@H]1CCCC[C@H]1NC>C1(C)C=CC=CC=1.C(Cl)Cl.CO.[Cu](I)I>[CH2:24]([O:31][C:32]1[CH:37]=[CH:36][N:35]([C:2]2[N:7]=[C:6]3[N:8]([CH3:23])[C:9]4[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:11](=[O:22])[C:10]=4[C:5]3=[CH:4][CH:3]=2)[C:34](=[O:38])[CH:33]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

9

Reactant 5

HCID 947Nitrogen2×HCID 10796Cesium carbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 86667083HCID 86667083, compound

Product 1

HCID 67970839HCID 67970839, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 1140TolueneSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
105 °C

Procedure

tert-Butyl 2-bromo-9-methyl-5-oxo-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridine-6-carboxylate (140 mg, 0.37 mmol), 4-benzyloxy pyridinone (74 mg, 0.37 mmol), and Cs2CO3 (132 mg, 0.41 mmol) were suspended in toluene (2 mL), and the air was removed under vacuum at −70° C. for 15 min. The system was flushed with N2, and trans-N,N′-dimethylcyclohexane-1,2-diamine (0.12 mL, 0.74 mmol) and copper iodide (140 mg, 0.74 mmol) were added to the suspension. The evacuation/N2 flushing process was repeated twice more, and the reaction mixture was heated at 105° C. for 18 h under N2. The mixture was cooled, diluted with 95:5 CH2Cl2/MeOH (12 mL), and washed with 2:1 brine/NH4OH (3×12 mL). The resulting organic solution was dried over Na2SO4, filtered, and concentrated to dryness under reduced pressure. The crude title compound was used in the next step without purification.

Workup

  1. customthe air was removed under vacuum at −70° C. for 15 min
  2. additionwere added to the suspension
  3. temperatureThe mixture was cooled
  4. washwashed with 2:1 brine/NH4OH (3×12 mL)
  5. dry with materialThe resulting organic solution was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe crude title compound was used in the next step without purification

Sources & evidence

ORD record
ord-a6ade3e116c94a5f9113d0136c338ac1
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

Loading…