Sodium Dithionite → 2-(4-((1h-Pyrazol-1-yl)methyl)phenyl)-6-chloro-7-(4-(pyridin-3-ylmethyl)piperazin-1-yl)-3h-imidazo[4,5-b]pyridine

HRID 416875

Reaction equation

HRID 416875 reaction equation
BrC1C(N2CCN(C(NC3C=CC=CC=3)=O)CC2)=C2N=C(C3C=CC(N(C)C)=CC=3)NC2=NC=1.[Cl: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+].[N:67]1([CH2:72][C:73]2[CH:80]=[CH:79][C:76]([CH:77]=O)=[CH:75][CH:74]=2)[CH:71]=[CH:70][CH:69]=[N:68]1>C(O)C.CN(C=O)C>[N:67]1([CH2:72][C:73]2[CH:80]=[CH:79][C:76]([C:77]3[NH:42][C:39]4=[N:40][CH:41]=[C:36]([Cl:35])[C:37]([N:46]5[CH2:51][CH2:50][N:49]([CH2:52][C:53]6[CH:54]=[N:55][CH:56]=[CH:57][CH:58]=6)[CH2:48][CH2:47]5)=[C:38]4[N:43]=3)=[CH:75][CH:74]=2)[CH:71]=[CH:70][CH:69]=[N:68]1

Participants

7

Reactant 4

HCID 24489Sodium DithioniteHCID 185258764-(1H-Pyrazol-1-ylmethyl)benzaldehydeHCID 578972325-Chloro-3-nitro-4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)pyridin-2-amineHCID 178482685HCID 178482685, compound

Product 1

HCID 1784782642-(4-((1h-Pyrazol-1-yl)methyl)phenyl)-6-chloro-7-(4-(pyridin-3-ylmethyl)piperazin-1-yl)-3h-imidazo[4,5-b]pyridineYield 29%

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-chloro-3-nitro-4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)pyridin-2-amine (12.5 mg, 0.036 mmol), DMF (0.10 mL), ethanol (0.70 mL), 1M Na2S2O4 (3 eq, 0.11 mmol, 0.11 mL) and 4-(1H-pyrazol-1-ylmethyl)benzaldehyde (1.1 eq, 0.039 mmol, 8 mg). After 6 h, concentration in vacuo and purification by preparative tlc (CH2Cl2-MeOH, 9:1) gave the product (5 mg, 29%) as a colourless solid; δH (500 MHz, DMSO-d6) 2.60 (s, br, 4H, piperazine N(CH2)2), 3.61 (s, 2H, NCH2), 3.70 (s, br, 4H, piperazine N(CH2)2), 5.41 (s, br, 2H, PhCH2), 6.30 (t, J=1.9 Hz, pyrazole H-4), 7.34 (d, J=8.4 Hz, 2H, phenyl H-3 & H-5), 7.37 (dd, J=7.6, 4.6 Hz, 1H, pyridine H-5), 7.49 (s, br, 1H, pyrazole H-3 or H-5), 7.78 (d, br, J=7.5 Hz, 1H, pyridine H-4), 7.86 (d, J=2.0 Hz, 1H, pyrazole H-3 or H-5), 8.11 (d, J=8.5 Hz, 2H, phenyl H-2 & H-6), 8.12 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.49 (dd, J=4.7 Hz, 1H, pyridine H-6), 8.56 (s, br, 1H, pyridine H-2), 13.47 (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-e160ab4e681343aa989b353bd8214bc7
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Linked notes

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