Acetonitrile → Diisopropylethylamine

HRID 602437Notes

Reaction equation

HRID 602437 reaction equation
Cl.CNOC.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:17]2C=CC=[CH:21][C:16]=2N=N1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:39]2C=CC=C[C:38]=2N=N1.Cl.[CH3:53]N(C)CCCN=C=NCC.[C:64](#[N:66])[CH3:65]>CN(C=O)C.C(N(CC)CC)C>[CH:64]([N:66]([CH:16]([CH3:21])[CH3:17])[CH2:38][CH3:39])([CH3:53])[CH3:65]

Participants

8

Reactant 5

HCID 6342AcetonitrileHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 81531Diisopropylethylamine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

The acid compound of formula (XXIII) is reacted with N,O-dimethylhydroxylamine hydrochloride in the presence of an amidation reagent such as 2-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorphosphate (HBTU), 2-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) or 1-(3-dimethylaminopropyI)-3-ethylcarbodiimide hydrochloride (EDC) and an organic base such as diisopropylethylamine or triethylamine in an aprotic organic solvent such as DMF or acetonitrile at room temperature to yield the compound of formula (XXII).

Sources & evidence

ORD record
ord-444d88c508c24c9c87c4c2d208843a2d
Source dataset
uspto-grants-2011_03
Patent number
US07906530B2

Reaction notes

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