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

HRID 416767Notes

Reaction equation

HRID 416767 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.Br[C:36]1C(N2CCN(CC)CC2)=C([N+]([O-])=O)C(N)=N[CH:41]=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[CH2:21][CH2:22][N:23]([CH2:36][CH3:41])[CH2:24][CH2:25]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 578972285-Bromo-4-(4-ethylpiperazin-1-yl)-3-nitropyridin-2-amineHCID 178482685HCID 178482685, compound

Product 1

HCID 1784626474-(6-Bromo-7-(4-ethylpiperazin-1-yl)-3h-imidazo[4,5-b]pyridin-2-yl)-n,n-dimethylanilineYield 49%

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-4-(4-ethylpiperazin-1-yl)-3-nitropyridin-2-amine (100 mg, 0.30 mmol), DMF (1.5 mL), 1M Na2S2O4 (3 eq, 0.90 mmol, 0.90 mL) and 4-(N,N-dimethylamino)benzaldehyde (1.05 eq, 0.32 mmol, 47 mg). After 18 h, filtration of the precipitate gave pure product (47 mg, 49%) as an off-white solid; 1H-NMR (500 MHz, DMSO-d6) 1.22 (br s, 3H, CH2CH3), 2.55 (s, 2H, CH2CH3), 2.73 (s, 2H, piperazine NCH2), 2.89 (s, 2H, piperazine NCH2), 3.01 (s, 6H, N(CH3)2), 3.80 (br s, 4H, piperazine N(CH2)2), 6.83 (d, J=8.9 Hz, 2H, N,N-dimethylaminophenyl), 8.02 (d, J=8.9 Hz, 2H, N,N-dimethylaminophenyl), 8.20 (s, 1H, imidazo[4,5-b]pyridine H-5), 13.23 (br s, 1H, imidazo[4,5-b]pyridine NH);

Workup

  1. customThis was prepared
  2. filtrationfiltration of the precipitate

Sources & evidence

ORD record
ord-39cae7e166374342b5a6f1b3070ca65a
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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