Acetic Acid → 2,4-Dimethoxybenzylamine

HRID 2230384Notes

Reaction equation

HRID 2230384 reaction equation
N1C=CC=N1.[C:6]1(=O)[NH:10][C:9](=O)[CH:8]=[CH:7]1.[H][H].Br[C:16]1[C:17]([O:19][C:20](=O)[CH:21]=1)=O.[C:23](O)(=[O:25])C>C(OC(=O)C)(=O)C>[CH3:23][O:25][C:16]1[CH:21]=[C:20]([O:19][CH3:17])[CH:6]=[CH:7][C:8]=1[CH2:9][NH2:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 800273-Bromo-2,5-furandioneHCID 22037740Maleimide pyrazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 5972502,4-Dimethoxybenzylamine

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Scheme C-6 illustrates the synthesis of the maleimide pyrazole scaffold C-63 wherein R4 is hydrogen. The synthesis starts with the condensation reaction of bromomaleic anhydride B77 with 2,4-dimethoxybenzylamine in acetic acid and acetic anhydride, giving rise to intermediate B78. The maleimide B78 is then treated with 4′-fluoroacetophenone in the presence of catalytic amount Pd2(dba)3 and sodium t-butoxide to form the fluoroacetophenone substituted maleimide B79. The B79 is treated with tert-butoxybis(dimethylamino)methane to yield the a-ketoenamine 80. The a-ketoenamine B80 is condensed with hydrazine to form the maleimide pyrazole skeleton B81. The 2,4-dimethoxybenzyl group protecting group is optionally removed with ceric ammonium nitrate (CAN) to give compound C-63.

Sources & evidence

ORD record
ord-e5540106d52b4f8185d30a619ba97e6d
Source dataset
uspto-grants-2002_07
Patent number
US06423713B1

Reaction notes

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