Pyrrole → Diisopropylamine

HRID 433884Notes

Reaction equation

HRID 433884 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C1C=C[C:9]2N(O)N=[N:12][C:10]=2[CH:11]=1>CN(C=O)C>[CH:3]([NH:12][CH:10]([CH3:9])[CH3:11])([CH3:4])[CH3:2].[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 8027PyrroleHCID 757711-Hydroxybenzotriazole

Product 2

HCID 7912DiisopropylamineHCID 8027Pyrrole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Chloropyrrolotriazine (1) (compound 3 of Scheme 9) can be reacted with an aniline (1a) (e.g., compound 1 of Scheme 11) in anhydrous DMF at rt to afford compound (2). Reaction of compound (2) with an aq. base such as NaOH with heating affords compound (3). Compound (3) can be reacted with an amine R2NH2 in the presence of a coupling reagent, such as HOBt, with or without a base such as diisopropylamine, in an organic solvent, such as DMF to afford compound (4). Compound (4) can be reacted with hydrogen in the presence of a catalyst, such as Pd/C, in an organic solvent, such as MeOH to afford compound (5). Reaction of compound (5) with an isocyanate in an organic solvent, such as DCE affords compound (6).

Sources & evidence

ORD record
ord-27b334296a8f480ea0080572d8fb7155
Source dataset
uspto-grants-2003_12
Patent number
US06670357B2

Reaction notes

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