Sodium Dithionite → HCID 178488864, compound

HRID 416854Notes

Reaction equation

HRID 416854 reaction equation
BrC1C(N2CCN(C(NC3C=CC=CC=3)=O)CC2)=C2N=C(C3C=CC(N(C)C)=CC=3)NC2=NC=1.[O:35]1[C:39]2[CH:40]=[CH:41][CH:42]=[C:43]([CH2:44][N:45]3[CH2:50][CH2:49][N:48]([C:51]4[C:56]([Br:57])=[CH:55][N:54]=[C:53]([NH2:58])[C:52]=4[N+:59]([O-])=O)[CH2:47][CH2:46]3)[C:38]=2[O:37][CH2:36]1.[O-]S(S([O-])=O)=O.[Na+].[Na+].[CH3:70][O:71][C:72]1[CH:77]=[CH:76][C:75]([CH:78]=O)=[CH:74][CH:73]=1>C(O)C.CN(C=O)C>[O:35]1[C:39]2[CH:40]=[CH:41][CH:42]=[C:43]([CH2:44][N:45]3[CH2:50][CH2:49][N:48]([C:51]4[C:56]([Br:57])=[CH:55][N:54]=[C:53]5[NH:58][C:78]([C:75]6[CH:76]=[CH:77][C:72]([O:71][CH3:70])=[CH:73][CH:74]=6)=[N:59][C:52]=45)[CH2:47][CH2:46]3)[C:38]=2[O:37][CH2:36]1

Participants

7

Reactant 4

HCID 24489Sodium DithioniteHCID 312444-MethoxybenzaldehydeHCID 57897141HCID 57897141, compoundHCID 178482685HCID 178482685, compound

Product 1

HCID 178488864HCID 178488864, compoundYield 63%

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 4-(4-(benzo[d][1,3]dioxol-4-ylmethyl)piperazin-1-yl)-5-bromo-3-nitropyridin-2-amine (30 mg, 0.068 mmol), DMF (0.15 mL), ethanol (0.85 mL), 1M Na2S2O4 (3 eq, 0.21 mmol, 0.21 mL) and 4-methoxybenzene carboxaldehyde (1.1 eq, 0.075 mmol, 10 mg). After 6 h, concentration in vacuo and purification by preparative tlc (CH2Cl2-MeOH, 95:5) gave the product (22 mg, 63%) as a colourless solid; δH (500 MHz, DMSO-d6) 2.63 (s, br, 4H, piperazine N(CH2)2), 3.55 (s, 2H, NCH2), 3.65 (t, J=4.3 Hz, 4H, piperazine N(CH2)2), 3.84 (s, 3H, OCH3), 6.02 (s, 2H, OCH2), 6.83 (d, J=4.2 Hz, 2H, benzo[d][1,3]dioxyl H-4 & H-6), 6.90 (app. q, J=4.4 Hz, 1H, benzo[d][1,3]dioxyl H-5), 7.09 (d, J=8.9 Hz, 2H, methoxyphenyl H-2 & H-6), 8.14 (d, J=8.9 Hz, 2H, methoxyphenyl H-3 & H-5), 8.20 (s, 1H, imidazo[4,5-b]pyridine H-5), 13.34 (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-6817deeeb8b848cdb46a072319c429e9
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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