Potassium Carbonate → HCID 24829800, compound

HRID 2245940Notes

Reaction equation

HRID 2245940 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([C:14]([C:17]4([C:20]5[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=5)[CH2:19][CH2:18]4)=[N:15][N:16]=3)[N:13]=2)=[CH:4][CH:3]=1.[NH:28]1[CH2:32][CH2:31][CH2:30][C:29]1=[O:33].CN[C@H]1CCCC[C@@H]1NC.C(=O)([O-])[O-].[K+].[K+].C(=O)=O.CC(C)=O>O1CCOCC1.[Cu]I>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([C:17]2([C:14]3[N:12]4[N:13]=[C:8]([C:5]5[CH:6]=[CH:7][C:2]([N:28]6[CH2:32][CH2:31][CH2:30][C:29]6=[O:33])=[CH:3][CH:4]=5)[CH:9]=[N:10][C:11]4=[N:16][N:15]=3)[CH2:19][CH2:18]2)=[CH:21][CH:22]=1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 120252-PyrrolidoneHCID 13822957(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamineHCID 18522661Acetone cardiceHCID 24831567HCID 24831567, compound

Product 1

HCID 24829800HCID 24829800, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 6-(4-bromophenyl)-3-[1-(4-methoxyphenyl)cyclopropyl][1,2,4]-triazolo[4,3-b][1,2,4]triazine (Example 17, isomer-I, 25.3 mg, 0.0600 mmol), 2-Pyrrolidinone (5.47 μL, 0.0720 mmol), (1S,2S)—N,N′-dimethylcyclohexane-1,2-diamine (1.9 μL, 0.012 mmol), copper(I) iodide (1.14 mg, 0.00600 mmol), and potassium carbonate (17.4 mg, 0.126 mmol) in 1,4-dioxane (0.75 mL) was cooled (dry-ice acetone bath), purged in vacuo, and charged with nitrogen. Then the mixture was heated at 150° C. for 4 h. After cooling, the mixture was diluted with methanol. The resulting solution was purified by RP-HPLC (pH=10) to give the desired product. Analytical LCMS: (M+H)+=427.1.

Workup

  1. custompurged in vacuo
  2. additioncharged with nitrogen
  3. temperatureAfter cooling
  4. additionthe mixture was diluted with methanol
  5. customThe resulting solution was purified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-6cb01e94a6154db9bc15bf16f784d28a
Source dataset
uspto-grants-2010_03
Patent number
US07683060B2

Reaction notes

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