Sodium Dithionite → HCID 178488871, compound

HRID 416828Notes

Reaction equation

HRID 416828 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][CH:56]=[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+].[CH3:67][O:68][C:69]1[N:74]=[CH:73][C:72]([CH:75]=O)=[CH:71][CH:70]=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][CH:56]=[CH:57][CH:58]=3)[CH2:48][CH2:47]2)=[C:38]2[N:43]=[C:75]([C:72]3[CH:73]=[N:74][C:69]([O:68][CH3:67])=[CH:70][CH:71]=3)[NH:42][C:39]2=[N:40][CH:41]=1

Participants

7

Reactant 4

HCID 24489Sodium DithioniteHCID 33645766-Methoxypyridine-3-carbaldehydeHCID 468687795-Bromo-3-nitro-4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)pyridin-2-amineHCID 178482685HCID 178482685, compound

Product 1

HCID 178488871HCID 178488871, compoundYield 34%

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-(pyridin-3-ylmethyl)piperazin-1-yl)pyridin-2-amine (75 mg, 0.19 mmol), DMF (0.15 mL), ethanol (0.85 mL), 1M Na2S2O4 (3 eq, 0.57 mmol, 0.57 mL) and 6-methoxy-3-pyridinecarboxaldehyde (1.1 eq, 0.21 mmol, 29 mg). After 6 h, concentration in vacuo and purification by preparative tlc (CH2Cl2-MeOH, 9:1) gave the product (31 mg, 34%) as a colourless solid; δH (500 MHz, DMSO-d6) 2.63 (br s, 4H, piperazine N(CH2)2), 3.62 (s, 2H, NCH2Ar), 3.68 (br s, 4H, piperazine N(CH2)2), 3.95 (s, 3H, OCH3), 7.00 (d, J=8.7 Hz, 1H, methoxypyridine H-5), 7.40 (dd, J=7.8, 4.8 Hz, 1H, pyridine H-5), 7.79 (d, br, J=7.8 Hz, 1H, pyridine H-4), 8.24 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.43 (dd, J=8.7, 2.3 Hz, 1H, methoxypyridine H-4), 8.50 (d, br, J=3.5 Hz, 1H, pyridine H-6), 8.57 (s, 1H, pyridine H-2), 8.96 (d, J=2.3 Hz, 1H, methoxypyridine H-2), 13.53 (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, 9:1)

Sources & evidence

ORD record
ord-1013fe4641144510ae9494bbb31de9df
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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