Triethylamine → 3-{(3R)-3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-6-yl)amino]piperidin-1-yl}-3-oxopropanenitrile

HRID 2192974Notes

Reaction equation

HRID 2192974 reaction equation
[Cl-].[F:2][C:3]1[CH:24]=[CH:23][C:6]2[C:7]([NH:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][NH2+:19][CH2:18]3)=[N:8][C:9]3[CH:10]=[CH:11][NH:12][C:13](=[O:15])[C:14]=3[C:5]=2[CH:4]=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:56]([CH2:58][C:59](O)=[O:60])#[N:57]>CN(C=O)C>[F:2][C:3]1[CH:24]=[CH:23][C:6]2[C:7]([NH:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][N:19]([C:59](=[O:60])[CH2:58][C:56]#[N:57])[CH2:18]3)=[N:8][C:9]3[CH:10]=[CH:11][NH:12][C:13](=[O:15])[C:14]=3[C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9740Cyanoacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67416365(3R)-3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-6-yl)amino]piperidinium chloride

Product 1

HCID 593753733-{(3R)-3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-6-yl)amino]piperidin-1-yl}-3-oxopropanenitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3R)-3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-6-yl)amino]piperidinium chloride (40 mg, 0.09 mmol) in DMF (2 mL) were added triethylamine (0.13 mL, 0.94 mmol), HATU (0-(7-Azabenzotriazol-1-yl)-N,N,N,N-tetramethyluronium hexafluorophosphate) (36 mg, 0.094 mmol), and cyanoacetic acid (40 mg, 0.47 mmol). The solution was stirred at room temperature overnight. The crude solution was filtered and purified by reverse phase HPLC. LRMS (ESI) calc'd for (C20H19FN5O2) [M+H]+, 380.2; found 380.1.

Workup

  1. filtrationThe crude solution was filtered
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-aff70e038aba467f9efc2a57f61b5e2b
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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