4-(Dimethylamino)Benzaldehyde → 1-(2-(4-(6-Bromo-2-(4-(dimethylamino)phenyl)-3H-imidazo[4,5-b]pyridin-7-yl)piperazin-1-yl)ethyl)-3-phenylurea

HRID 416760Notes

Reaction equation

HRID 416760 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.NC1C([N+]([O-])=O)=C(N2CCN([CH2:51][CH2:52][NH:53][C:54]([NH:56][C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)=[O:55])CC2)C(Br)=CN=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]([CH2:51][CH2:52][NH:53][C:54]([NH:56][C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)=[O:55])[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 578972931-(2-(4-(2-Amino-5-bromo-3-nitropyridin-4-yl)piperazin-1-yl)ethyl)-3-phenylureaHCID 178482685HCID 178482685, compound

Product 1

HCID 1784826721-(2-(4-(6-Bromo-2-(4-(dimethylamino)phenyl)-3H-imidazo[4,5-b]pyridin-7-yl)piperazin-1-yl)ethyl)-3-phenylurea

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 1-(2-(4-(2-amino-5-bromo-3-nitropyridin-4-yl)piperazin-1-yl)ethyl)-3-phenylurea (100 mg, 0.22 mmol), DMF (1.25 mL), 1M Na2S2O4 (3 eq, 0.66 mmol, 0.66 mL) and 4-(N,N-dimethylamino)benzaldehyde (1.05 eq, 0.23 mmol, 34 mg). After filtration, a small sample of the solid product was further purified by semi-preparative hplc to give the pure product as an off-white solid; 1H-NMR (500 MHz, DMSO-d6) 2.50 (2H, obscured by DMSO peak, NCH2), 2.53-2.57 (m, 4H, piperazine N(CH2)2), 3.00 (s, 6H, N(CH3)2), 3.27 (q, J=5.7 Hz, 2H, NHCH2), 3.67 (t, J=4.6 Hz, 4H, piperazine N(CH2)2), 6.13 (t, br, J=5.0 Hz, 1H, NHCH2), 6.82 (d, J=9.0 Hz, 2H, N,N-dimethylaminophenyl), 6.88 (tt, J=7.4, 1.0 Hz, 1H, phenyl H-4), 7.22 (dd, J=8.4, 7.5 Hz, 2H, phenyl H-3 & H-5), 7.40 (dd, J=8.5, 1.0 Hz, 2H, phenyl H-3 & H-5), 8.01 (d, J=8.9 Hz, 2H, N,N-dimethylaminophenyl), 8.16 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.64 (br s, 1H, PhNH), 13.13 (br s, 1H, imidazo[4,5-b]pyridine NH);

Workup

  1. customThis was prepared
  2. filtrationAfter filtration
  3. customa small sample of the solid product was further purified by semi-preparative hplc

Sources & evidence

ORD record
ord-4853c43aa2e145fbadb0e151ab5b2f6b
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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