Ethyl 7-(4-methoxybenzyl)-1-methyl-2,8-dioxo-1,2,7,8-tetrahydropyrido[2,3-d]pyridazine-3-carboxylate → Ethyl 1-methyl-2,8-dioxo-1,2,7,8-tetrahydropyrido[2,3-d]pyridazine-3-carboxylate

HRID 1966384Notes

Reaction equation

HRID 1966384 reaction equation
COC1C=CC(C[N:8]2[C:13](=[O:14])[C:12]3[N:15]([CH3:25])[C:16](=[O:24])[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:18][C:11]=3[CH:10]=[N:9]2)=CC=1>C(O)(C(F)(F)F)=O>[CH3:25][N:15]1[C:12]2[C:13](=[O:14])[NH:8][N:9]=[CH:10][C:11]=2[CH:18]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:16]1=[O:24]

Participants

3

Reactant 1

HCID 46930534Ethyl 7-(4-methoxybenzyl)-1-methyl-2,8-dioxo-1,2,7,8-tetrahydropyrido[2,3-d]pyridazine-3-carboxylate

Product 1

HCID 66988436Ethyl 1-methyl-2,8-dioxo-1,2,7,8-tetrahydropyrido[2,3-d]pyridazine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of ethyl 7-(4-methoxybenzyl)-1-methyl-2,8-dioxo-1,2,7,8-tetrahydropyrido[2,3-d]pyridazine-3-carboxylate (5) (2.45 g, 6.63 mmol) in TFA (15 mL) was heated in a microwave at 125° C. for 150 min, then cooled to RT. The volatiles were removed in vacuo to give crude ethyl 1-methyl-2,8-dioxo-1,2,7,8-tetrahydropyrido[2,3-d]pyridazine-3-carboxylate which was used directly in the next step.

Workup

  1. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-3594ce1ab2a24839a7d2e761e2ea6b38
Source dataset
uspto-grants-2013_04
Patent number
US08420649B2

Reaction notes

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