4-(Dimethylamino)Benzaldehyde → HCID 178482664, compound

HRID 416769Notes

Reaction equation

HRID 416769 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([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)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]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[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

6

Reactant 4

HCID 74794-(Dimethylamino)BenzaldehydeHCID 24489Sodium DithioniteHCID 468683475-Bromo-3-nitro-4-(4-phenylpiperazin-1-yl)pyridin-2-amineHCID 178482685HCID 178482685, compound

Product 1

HCID 178482664HCID 178482664, compoundYield 36%

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-phenylpiperazin-1-yl)pyridin-2-amine (75 mg, 0.20 mmol), DMF (1.5 mL), 1M Na2S2O4 (3 eq, 0.60 mmol, 0.60 mL) and 4-(N,N-dimethylamino)benzaldehyde (1.05 eq, 0.21 mmol, 31 mg). After 18 h, filtration of the precipitate and trituration with Et2O gave the product (34 mg, 36%) as a pale yellow solid; 1H-NMR (500 MHz, DMSO-d6) 3.00 (s, 6H, N(CH3)2), 3.36-3.38 (m, 4H, piperazine N(CH2)2), 3.78-3.80 (m, 4H, piperazine N(CH2)2), 6.80-6.83 (m, 1H, phenyl H-4), 6.82 (d, J=8.7 Hz, 2H, N,N-dimethylaminophenyl), 7.03 (d, J=8.0 Hz, 2H, phenyl H-2 & H-6), 7.25 (t, br, J=8.0 Hz, 2H, phenyl H-3 & H-5), 8.02 (d, J=8.8 Hz, 2H, N,N-dimethylaminophenyl), 8.19 (s, 1H, imidazo[4,5-b]pyridine H-5), 13.14 (s, br, 1H, imidazo[4,5-b]pyridine NH);

Workup

  1. customThis was prepared
  2. filtrationfiltration of the precipitate and trituration with Et2O

Sources & evidence

ORD record
ord-080c5c97ea7b4cb889cc78b115af53be
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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