Sodium Dithionite → HCID 178453047, compound

HRID 416826Notes

Reaction equation

HRID 416826 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+].[CH:67]([C:69]1[CH:70]=[C:71]([CH:81]=[CH:82][CH:83]=1)[CH2:72][NH:73][C:74](=[O:80])[O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=O>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:67]([C:69]3[CH:70]=[C:71]([CH:81]=[CH:82][CH:83]=3)[CH2:72][NH:73][C:74](=[O:80])[O:75][C:76]([CH3:79])([CH3:77])[CH3:78])[NH:42][C:39]2=[N:40][CH:41]=1

Participants

7

Reactant 4

HCID 24489Sodium DithioniteHCID 2794834tert-Butyl 3-formylbenzylcarbamateHCID 468687795-Bromo-3-nitro-4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)pyridin-2-amineHCID 178482685HCID 178482685, compound

Product 1

HCID 178453047HCID 178453047, compoundYield 73.3%

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 (200 mg, 0.51 mmol), DMF (0.45 mL), ethanol (2.55 mL), 1M Na2S2O4 (3 eq, 1.53 mmol, 1.53 mL) and tert-butyl N-(3-formylbenzyl)carbamate (1.1 eq, 0.21 mmol, 132 mg). After 18 h, concentration in vacuo and column chromatography (CH2Cl2-MeOH, 95:5) gave the product (89 mg, 30%) as a colourless solid; δH (500 MHz, DMSO-d6) 1.38 (s, 9H, C(CH3)3), 2.62 (s, br, 4H, piperazine N(CH2)2), 3.61 (s, 2H, NCH2Ar), 3.66 (s, br, 4H, piperazine N(CH2)2), 4.22 (d, J=6.0 Hz, 2H, CH2NH—BOC), 7.36 (d, J=7.7 Hz, 1H, phenyl H-4 or H-6), 7.39 (dd, J=7.7, 2.7 Hz, 1H, pyridine H-5), 7.45 (t, br, J=5.7 Hz, 1H, NH—BOC), 7.48 (t, J=7.7 Hz, 1H, phenyl H-5), 7.78 (d, J=7.6 Hz, 1H, pyridine H-4), 8.01 (d, J=7.7 Hz, 1H, phenyl H-4 or H-6), 8.10 (s, br, 1H, phenyl H-2), 8.25 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.50 (d, br, J=3.5 Hz, 1H, pyridine H-6), 8.57 (s, br, 1H, pyridine H-2), 13.52 (s, br, 1H, imidazo[4,5-b]pyridine NH);

Workup

  1. customThis was prepared
  2. concentrationconcentration in vacuo and column chromatography (CH2Cl2-MeOH, 95:5)

Sources & evidence

ORD record
ord-899bef4783974f43b11af5e755bdf80e
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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