Sodium Dithionite → Tert-butyl 4-(6-bromo-7-(4-(pyridin-3-ylmethyl)piperazin-1-yl)-3h-imidazo[4,5-b]pyridin-2-yl)benzylcarbamate

HRID 416786Notes

Reaction equation

HRID 416786 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:83]=[CH:82][C:72]([CH2:73][NH:74][C:75](=[O:81])[O:76][C:77]([CH3:80])([CH3:79])[CH3:78])=[CH:71][CH:70]=1)=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:83]=[CH:82][C:72]([CH2:73][NH:74][C:75](=[O:81])[O:76][C:77]([CH3:80])([CH3:78])[CH3:79])=[CH:71][CH:70]=3)[NH:42][C:39]2=[N:40][CH:41]=1

Participants

7

Reactant 4

HCID 24489Sodium DithioniteHCID 2794832tert-Butyl hydrogen ((4-formylphenyl)methyl)carbonimidateHCID 468687795-Bromo-3-nitro-4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)pyridin-2-amineHCID 178482685HCID 178482685, compound

Product 1

HCID 178453034Tert-butyl 4-(6-bromo-7-(4-(pyridin-3-ylmethyl)piperazin-1-yl)-3h-imidazo[4,5-b]pyridin-2-yl)benzylcarbamateYield 65%

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 (2.55 mL), ethanol (0.45 mL), 1M Na2S2O4 (3 eq, 1.53 mmol, 1.53 mL) and tert-butyl N-(4-formylbenzyl)carbamate (1.1 eq, 0.21 mmol, 46 mg). After 18 h, filtration of the precipitate and washing with cold water (1 mL) gave the product (79 mg, 27%) as a colourless solid; 1H-NMR (500 MHz, DMSO-d6) 1.41 (s, 9H, C(CH3)3), 2.63-2.76 (m, 2H, piperazine NCH2), 2.89 (s, 2H, piperazine NCH2), 3.71-3.77 (m, 6H, piperazine N(CH2)2 & NCH2Ar), 4.19 (d, J=5.8 Hz, 2H, CH2NH—BOC), 7.39 (d, J=8.1 Hz, 2H, phenyl H-2 & H-6), 7.40-7.44 (m, 1H, pyridine H-5), 7.82 (s, br, 1H, pyridine H-4), 7.95 (s, br, 1H, NH—BOC), 8.12 (d, J=8.1 Hz, 2H, phenyl H-3 & H-5), 8.25 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.53 (br s, 1H, pyridine H-6), 8.60 (s, br, 1H, pyridine H-2), 13.49 (br s, 1H, imidazo[4,5-b]pyridine NH);

Workup

  1. customThis was prepared
  2. filtrationfiltration of the precipitate
  3. washwashing with cold water (1 mL)

Sources & evidence

ORD record
ord-0a62d19c04ea4d00baed6b8eaa0db48d
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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