Iodo benzene diacetate → Methyl 4-[3-(1-quinolin-6-ylcyclopropyl) [1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzoate

HRID 1099077Notes

Reaction equation

HRID 1099077 reaction equation
[NH:1]([C:3]1[N:4]=[N:5][C:6]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[CH:7][N:8]=1)[NH2:2].[N:19]1[C:28]2[C:23](=[CH:24][C:25]([C:29]3([CH:32]=O)[CH2:31][CH2:30]3)=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(O)C.C(O)(=O)C>[N:19]1[C:28]2[C:23](=[CH:24][C:25]([C:29]3([C:32]4[N:4]5[N:5]=[C:6]([C:9]6[CH:10]=[CH:11][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:17][CH:18]=6)[CH:7]=[N:8][C:3]5=[N:1][N:2]=4)[CH2:31][CH2:30]3)=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 12217721Iodo benzene diacetateHCID 592162771-Quinolin-6-ylcyclopropanecarbaldehydeHCID 59216328Methyl 4-(3-hydrazino-1,2,4-triazin-6-yl)benzoate

Product 1

HCID 59216329Methyl 4-[3-(1-quinolin-6-ylcyclopropyl) [1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzoateYield 60.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of methyl 4-(3-hydrazino-1,2,4-triazin-6-yl)benzoate (115 mg, 0.000469 mol) and 1-quinolin-6-ylcyclopropanecarbaldehyde (92 mg, 0.00047 mol) in ethanol (2 mL) and acetic acid (0.5 mL) was stirred at RT for 6 h. The volatiles were removed under reduced pressure. The residue was dried under high vacuum, and then dissolved in methylene chloride (6 mL). To the solution was added iodobenzene diacetate (180 mg, 0.00056 mol). The reaction mixture was stirred at RT overnight. The solvent was evaporated and the residue was flash chromatographed on a silica gel column to afford the desired product (120 mg, 60%). Analytical LCMS: (M+H)+=423.3.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customThe residue was dried under high vacuum
  3. dissolutiondissolved in methylene chloride (6 mL)
  4. stirringThe reaction mixture was stirred at RT overnight
  5. customThe solvent was evaporated
  6. customchromatographed on a silica gel column

Sources & evidence

ORD record
ord-61985aac30cb49bab38e56c45214d3e8
Source dataset
uspto-grants-2012_03
Patent number
US08143251B2

Reaction notes

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