Pyrazole → HCID 59216289, compound

HRID 1099071Notes

Reaction equation

HRID 1099071 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:21]=[C:22]6[C:27](=[CH:28][CH:29]=5)[N:26]=[CH:25][CH:24]=[CH:23]6)[CH2:19][CH2:18]4)=[N:15][N:16]=3)[N:13]=2)=[CH:4][CH:3]=1.[NH:30]1[CH:34]=[CH:33][CH:32]=[N:31]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNC1CCCCC1NC>O1CCOCC1.CO.[Cu]I>[N:30]1([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:9]=[N:10][C:11]4[N:12]([C:14]([C:17]5([C:20]6[CH:21]=[C:22]7[C:27](=[CH:28][CH:29]=6)[N:26]=[CH:25][CH:24]=[CH:23]7)[CH2:19][CH2:18]5)=[N:15][N:16]=4)[N:13]=3)=[CH:4][CH:3]=2)[CH:34]=[CH:33][CH:32]=[N:31]1

Participants

8

Reactant 4

HCID 1048PyrazoleHCID 62657Potassium Phosphate, TribasicHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 24829630HCID 24829630, compound

Product 1

HCID 59216289HCID 59216289, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 6-{1-[6-(4-bromophenyl) [1,2,4]triazolo[4,3-b][1,2,4]triazin-3-yl]cyclopropyl}quinoline (20 mg, 0.04 mmol, Example 41), 1H-pyrazole (4.6 mg, 0.068 mmol), potassium phosphate (20 mg, 0.095 mmol), N,N′-dimethylcyclohexane-1,2-diamine (1.4 μL), and copper(I) iodide (1.7 mg) in 1,4-dioxane (500 μL) was heated at 150° C. for 2 h. After cooling, the mixture was diluted with methanol and filtered. The filtrate was purified by RP-HPLC (pH=10) to afford the desired product. Analytical LCMS: (M+H)+=431.1.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered
  3. customThe filtrate was purified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-58ccac56940441ce964f190108a83e43
Source dataset
uspto-grants-2012_03
Patent number
US08143251B2

Reaction notes

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