4-(Dimethylamino)Benzaldehyde → 4-(6-Bromo-7-(4-(methylsulfonyl)piperazin-1-yl)-3h-imidazo[4,5-b]pyridin-2-yl)-n,n-dimethylaniline

HRID 416771Notes

Reaction equation

HRID 416771 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]([CH3:55])(=[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>C(O)C.CN(C=O)C>[Br:1][C:2]1[C:3]([N:20]2[CH2:25][CH2:24][N:23]([S:52]([CH3:55])(=[O:54])=[O:53])[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

Participants

7

Reactant 4

HCID 74794-(Dimethylamino)BenzaldehydeHCID 24489Sodium DithioniteHCID 578973105-Bromo-4-(4-(methylsulfonyl)piperazin-1-yl)-3-nitropyridin-2-amineHCID 178482685HCID 178482685, compound

Product 1

HCID 1784826884-(6-Bromo-7-(4-(methylsulfonyl)piperazin-1-yl)-3h-imidazo[4,5-b]pyridin-2-yl)-n,n-dimethylanilineYield 39%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 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-4-(4-(methylsulfonyl)piperazin-1-yl)-3-nitropyridin-2-amine (100 mg, 0.26 mmol), DMF (1.6 mL), ethanol (0.2 mL), 1M Na2S2O4 (4 eq, 1.05 mmol, 1.05 mL) and 4-(N,N-dimethylamino)benzaldehyde (1.1 eq, 0.29 mmol, 43 mg). After 6 h, filtration of the precipitate and washing with cold ethanol (1 mL) and cold water (1 mL) gave the product (49 mg, 39%) as a pale yellow solid; 1H-NMR (500 MHz, DMSO-d6) 2.97 (s, 3H, SO2CH3), 3.01 (s, 6H, N(CH3)2), 3.34-3.38 (m, 4H, piperazine N(CH2)2), 3.70-3.73 (m, 4H, piperazine N(CH2)2), 6.83 (d, J=9.0 Hz, 2H, N,N-dimethylaminophenyl) 8.05 (d, J=8.9 Hz, 2H, N,N-dimethylaminophenyl), 8.21 (s, 1H, imidazo[4,5-b]pyridine H-5), 13.21 (br s, 1H, imidazo[4,5-b]pyridine NH);

Workup

  1. customThis was prepared
  2. filtrationfiltration of the precipitate
  3. washwashing with cold ethanol (1 mL) and cold water (1 mL)

Sources & evidence

ORD record
ord-b9b0fad001154bf4bc86fd8a6bd3ab2b
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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