4-(Dimethylamino)Benzaldehyde → 4-(6-Bromo-7-(4-(phenylsulfonyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)-N,N-dimethylaniline

HRID 416758Notes

Reaction equation

HRID 416758 reaction equation
[Br:1][C:2]1[C:3]([N:20]2[CH2:25][CH2:24][N:23](C(NC3C=CC=CC=3)=O)[CH2:22][CH2:21]2)=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.BrC1C(N2CCN([S:52]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)(=[O:54])=[O:53])CC2)=C([N+]([O-])=O)C(N)=NC=1.[O-]S(S([O-])=O)=O.[Na+].[Na+].CN(C1C=CC(C=O)=CC=1)C>CN(C=O)C>[Br:1][C:2]1[C:3]([N:20]2[CH2:25][CH2:24][N:23]([S:52]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)(=[O:54])=[O:53])[CH2:22][CH2:21]2)=[C:4]2[N:10]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([N:17]([CH3:18])[CH3:19])=[CH:15][CH:16]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 74794-(Dimethylamino)BenzaldehydeHCID 24489Sodium DithioniteHCID 468683465-Bromo-3-nitro-4-(4-(phenylsulfonyl)piperazin-1-yl)pyridin-2-amineHCID 178482685HCID 178482685, compound

Product 1

HCID 1784826894-(6-Bromo-7-(4-(phenylsulfonyl)piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)-N,N-dimethylanilineYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This was prepared using the same procedure as for 4-(6-bromo-2-(4-(dimethylamino)phenyl)-3H-imidazo[4,5-b]pyridin-7-yl)-N-phenylpiperazine-1-carboxamide, but here using 5-bromo-3-nitro-4-(4-(phenylsulfonyl)piperazin-1-yl)pyridin-2-amine (40 mg, 0.090 mmol), DMF (1 mL), 1M Na2S2O4 (3 eq, 0.27 mmol, 0.27 mL) and 4-(N,N-dimethylamino)benzaldehyde (1.1 eq, 0.099 mmol, 15 mg). After 18 h, the reaction was quenched with NH4OH and extracted with EtOAc (5×5 mL). The organic extracts were dried (MgSO4), filtered and concentrated in vacuo to give the product (11 mg, 23%) as a pale yellow solid; 1H-NMR (500 MHz, DMSO-d6) 3.01 (s, 6H, N(CH3)2), 3.17-3.27 (m, 4H, piperazine N(CH2)2), 3.65 (t, J=4.7 Hz, 4H, piperazine N(CH2)2), 6.82 (d, J=9.0 Hz, 2H, N,N-dimethylaminophenyl), 7.68-7.70 (m, 2H, phenyl H-3 & H-5), 7.73-7.76 (m, 1H, phenyl H-4), 7.81 (dd, J=7.1, 1.5 Hz, 2H, phenyl H-2 & H-6), 7.99 (d, J=9.0, 2H, N,N-dimethylaminophenyl), 8.14 (s, 1H, imidazo[4,5-b]pyridine H-5), 13.21 (s, br, 1H, imidazo[4,5-b]pyridine NH);

Workup

  1. customThis was prepared
  2. customthe reaction was quenched with NH4OH
  3. extractionextracted with EtOAc (5×5 mL)
  4. dry with materialThe organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3a53fdb76a5940678e0e3e04f0406760
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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