Isoindoline → Methyl 6-(isoindoline-2-carboxamido)pyridazine-3-carboxylate

HRID 624207Notes

Reaction equation

HRID 624207 reaction equation
[N:1]([C:4]1[N:9]=[N:8][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1)=[C:2]=[O:3].[CH2:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][NH:15]1>C1COCC1>[CH2:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][N:15]1[C:2]([NH:1][C:4]1[N:9]=[N:8][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 422478IsoindolineHCID 86665081Methyl 6-isocyanatopyridazine-3-carboxylate

Product 1

HCID 68753001Methyl 6-(isoindoline-2-carboxamido)pyridazine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 6-isocyanatopyridazine-3-carboxylate (5.26 g, 29.4 mmol) in THF (100 mL), a solution of isoindoline (5.24 g, 4.41 mmol) in THF (50 mL) was added at 0° C. The reaction mixture was stirred overnight at room temperature. The reaction mixture was filtered and the precipitate was washed with cold EtOAc and dried in high vacuum to give the title compound as a solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe precipitate was washed with cold EtOAc
  3. customdried in high vacuum

Sources & evidence

ORD record
ord-696935afcc774c6889224e2bc60d9fa4
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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