HCID 69030337, compound → HCID 86596910, compound

HRID 2251831Notes

Reaction equation

HRID 2251831 reaction equation
NC1N=CC=C2C=1N[C:8](=[O:11])C2.[F:12][C:13]1[N:27]=[CH:26][CH:25]=[CH:24][C:14]=1[C:15]([N:17]([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])=[O:16]>>[CH:8]([C:24]1[C:14]([C:15]([N:17]([CH:18]([CH3:19])[CH3:20])[CH:21]([CH3:22])[CH3:23])=[O:16])=[C:13]([F:12])[N:27]=[CH:26][CH:25]=1)=[O:11]

Participants

3

Reactant 2

HCID 69030337HCID 69030337, compoundHCID 69031022HCID 69031022, compound

Product 1

HCID 86596910HCID 86596910, compound

Procedure

The 7-amino-6-aza-oxindole 16 can also be prepared by lithiation of 2-fluoro-N,N-diisopropylnicotinamide 17 followed by quenching, such as with DMF, to give the 4-formyl-2-fluoro-N,N-diisopropylnicotinamide 18. The 4-formyl-2-fluoro-N,N-diisopropylnicotinamide can be reacted with an amine to give the 4-aminomethyl-2-fluoro-N,N-diisopropylnicotinamide 19 which can be reacted with another amine then cyclized under acidic conditions to afford the 7-amino-6-aza-oxindole 16.

Workup

  1. customby quenching, such as with DMF

Sources & evidence

ORD record
ord-24de0e0031fb4deb858d882fb469072a
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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