Sodium Dithionite → HCID 178488876, compound

HRID 416864Notes

Reaction equation

HRID 416864 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[C:54]([CH3:59])=[N:55][O:56][C:57]=3[CH3:58])[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+].[CH3:68][O:69][C:70]1[CH:75]=[CH:74][C:73]([CH:76]=O)=[CH:72][CH:71]=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[C:54]([CH3:59])=[N:55][O:56][C:57]=3[CH3:58])[CH2:48][CH2:47]2)=[C:38]2[N:43]=[C:76]([C:73]3[CH:74]=[CH:75][C:70]([O:69][CH3:68])=[CH:71][CH:72]=3)[NH:42][C:39]2=[N:40][CH:41]=1

Participants

7

Reactant 4

HCID 24489Sodium DithioniteHCID 312444-MethoxybenzaldehydeHCID 57897287HCID 57897287, compoundHCID 178482685HCID 178482685, compound

Product 1

HCID 178488876HCID 178488876, compoundYield 42%

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-((3,5-dimethylisoxazol-4-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine (20 mg, 0.049 mmol), DMF (0.15 mL), ethanol (0.85 mL), 1M Na2S2O4 (3 eq, 0.14 mmol, 0.14 mL) and 4-methoxybenzene carboxaldehyde (1.1 eq, 0.053 mmol, 7 mg). After 6 h, concentration in vacuo and purification by preparative tlc (CH2Cl2-MeOH, 95:5) gave the product (10 mg, 42%) as a colourless solid; δH (500 MHz, DMSO-d6) 2.26 (s, 3H, CH3), 2.39 (s, 3H, CH3), 2.63 (t, J=4.6 Hz, 4H, piperazine N(CH2)2), 3.40 (s, 2H, CH2), 3.72 (s, br, 4H, piperazine N(CH2)2), 3.88 (s, 3H, OCH3), 7.08 (d, J=8.8 Hz, 2H, methoxyphenyl H-2 & H-6), 8.12 (d, J=8.7 Hz, 2H, methoxyphenyl H-3 & H-5), 8.21 (s, 1H, imidazo[4,5-b]pyridine H-5), 13.03 (s, br, 1H, imidazo[4,5-b]pyridine NH); LC (Method B)-MS (ESI, m/z): Rt=3.29 min—497, 499 [(M+H)+, Br isotopic pattern]. ESI-HRMS: Found: 497.1301, calculated for C23H25BrN6O2 (M+H)+: 497.1301.

Workup

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

Sources & evidence

ORD record
ord-9dcd254ec65b4a49b8d5cf75ad065c3a
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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