Sodium Dithionite → HCID 178488865, compound

HRID 416860Notes

Reaction equation

HRID 416860 reaction equation
BrC1C(N2CCN(C(NC3C=CC=CC=3)=O)CC2)=C2N=C(C3C=CC(N(C)C)=CC=3)NC2=NC=1.[Br:35][C:36]1[C:37]([N:46]2[CH2:51][CH2:50][N:49]([CH2:52][C:53]3[CH:54]=[N:55][C:56]([C:59]([F:62])([F:61])[F:60])=[CH:57][CH:58]=3)[CH2:48][CH2:47]2)=[C:38]([N+:43]([O-])=O)[C:39]([NH2:42])=[N:40][CH:41]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+].[CH3:71][O:72][C:73]1[CH:78]=[CH:77][C:76]([CH:79]=O)=[CH:75][CH:74]=1>C(O)C.CN(C=O)C>[Br:35][C:36]1[C:37]([N:46]2[CH2:51][CH2:50][N:49]([CH2:52][C:53]3[CH:54]=[N:55][C:56]([C:59]([F:62])([F:61])[F:60])=[CH:57][CH:58]=3)[CH2:48][CH2:47]2)=[C:38]2[N:43]=[C:79]([C:76]3[CH:77]=[CH:78][C:73]([O:72][CH3:71])=[CH:74][CH:75]=3)[NH:42][C:39]2=[N:40][CH:41]=1

Participants

7

Reactant 4

HCID 24489Sodium DithioniteHCID 312444-MethoxybenzaldehydeHCID 57897304HCID 57897304, compoundHCID 178482685HCID 178482685, compound

Product 1

HCID 178488865HCID 178488865, compoundYield 52%

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-3-nitro-4-(4-((6-(trifluoromethyl)pyridin-3-yl)methyl)piperazin-1-yl)pyridin-2-amine (20 mg, 0.043 mmol), DMF (0.15 mL), ethanol (0.85 mL), 1M Na2S2O4 (3 eq, 0.13 mmol, 0.13 mL) and 4-methoxybenzene carboxaldehyde (1.1 eq, 0.048 mmol, 6.5 mg). After 6 h, concentration in vacuo and purification by preparative tlc (CH2Cl2-MeOH, 95:5) gave the product (10 mg, 52%) as a colourless solid; δH (500 MHz, DMSO-d6) 2.64 (s, br, 4H, piperazine N(CH2)2), 3.67 (s, br, 4H, piperazine N(CH2)2), 3.73 (s, 2H, NCH2), 3.84 (s, 3H, OCH3), 7.10 (d, J=8.8 Hz, 2H, methoxyphenyl H-2 & H-6), 7.91 (d, br, J=7.6 Hz, 1H, pyridine H-5), 8.09 (d, br, J=7.7 Hz, 1H, pyridine H-4), 8.13 (d, J=8.7 Hz, 2H, methoxyphenyl H-3 & H-5), 8.21 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.77 (s, br, 1H, pyridine H-2), 13.58 (s, br, 1H, imidazo[4,5-b]pyridine NH);

Workup

  1. customThis was prepared
  2. concentrationconcentration
  3. customin vacuo and purification by preparative tlc (CH2Cl2-MeOH, 95:5)

Sources & evidence

ORD record
ord-ebbf2e33dbe24d73a7943946e0cea067
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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