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

HRID 1099092Notes

Reaction equation

HRID 1099092 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([C:12]2[N:17]=[N:16][C:15]([NH:18][NH2:19])=[N:14][CH:13]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[N:20]1[C:29]2[C:24](=[CH:25][C:26]([C:30]3([CH:33]=O)[CH2:32][CH2:31]3)=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(O)C.C(O)(=O)C>[F:1][C:2]1[CH:11]=[C:10]([C:12]2[CH:13]=[N:14][C:15]3[N:16]([C:33]([C:30]4([C:26]5[CH:25]=[C:24]6[C:29](=[CH:28][CH:27]=5)[N:20]=[CH:21][CH:22]=[CH:23]6)[CH2:32][CH2:31]4)=[N:19][N:18]=3)[N:17]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 12217721Iodo benzene diacetateHCID 592162771-Quinolin-6-ylcyclopropanecarbaldehydeHCID 59216321Methyl 2-fluoro-4-(3-hydrazino-1,2,4-triazin-6-yl)benzoate

Product 1

HCID 59216283Methyl 2-fluoro-4-[3-(1-quinolin-6-ylcyclopropyl) [1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl]benzoateYield 53.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of methyl 2-fluoro-4-(3-hydrazino-1,2,4-triazin-6-yl)benzoate (0.17 g, 0.64 mmol) and 1-quinolin-6-ylcyclopropanecarbaldehyde (0.13 g, 0.64 mmol) in ethanol (10 mL) and acetic acid (1 mL) was stirred at RT for 2 h. The mixture was concentrated. The residue was dissolved in methylene chloride (5 mL). To the solution was added iodobenzene diacetate (230 mg, 0.71 mmol) with stirring. The mixture was stirred at RT for 2 h then concentrated. The residue was flash chromatographed on a silica gel column to give the desired product (150 mg). Analytical LCMS: (M+H)+=441.0.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionThe residue was dissolved in methylene chloride (5 mL)
  3. stirringwith stirring
  4. stirringThe mixture was stirred at RT for 2 h
  5. concentrationthen concentrated
  6. customchromatographed on a silica gel column

Sources & evidence

ORD record
ord-98ff4c7bbd8446119677c84c620e8375
Source dataset
uspto-grants-2012_03
Patent number
US08143251B2

Reaction notes

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