Sodium Dithionite → HCID 178452226, compound

HRID 416836Notes

Reaction equation

HRID 416836 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+].[C:67]([O:71][C:72]([N:74]1[CH2:79][CH2:78][N:77]([C:80]2[CH:85]=[CH:84][C:83]([CH:86]=O)=[CH:82][CH:81]=2)[CH2:76][CH2:75]1)=[O:73])([CH3:70])([CH3:69])[CH3:68]>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:86]([C:83]3[CH:82]=[CH:81][C:80]([N:77]4[CH2:76][CH2:75][N:74]([C:72]([O:71][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:73])[CH2:79][CH2:78]4)=[CH:85][CH:84]=3)[NH:42][C:39]2=[N:40][CH:41]=1

Participants

7

Reactant 4

HCID 24489Sodium DithioniteHCID 2795509Tert-butyl 4-(4-formylphenyl)piperazine-1-carboxylateHCID 468687795-Bromo-3-nitro-4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)pyridin-2-amineHCID 178482685HCID 178482685, compound

Product 1

HCID 178452226HCID 178452226, compoundYield 31%

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 (50 mg, 0.13 mmol), DMF (0.3 mL), ethanol (1.2 mL), 1M Na2S2O4 (3 eq, 0.38 mmol, 0.38 mL) and 4-(4-formylphenyl)piperazine-1-carboxylic acid tert-butyl ester (1.1 eq, 0.14 mmol, 43 mg). After 6 h, concentration in vacuo and purification by preparative tlc (CH2Cl2-MeOH, 95:5) gave the product (25 mg, 31%) as an off-white solid; δH (500 MHz, DMSO-d6) 1.43 (s, 9H, C(CH3)3), 2.61 (s, br, 4H, piperazine N(CH2)2), 3.26 (s, br, 4H, piperazine N(CH2)2), 3.48 (t, J=4.6 Hz, 4H, piperazine N(CH2)2), 3.61 (s, 2H, CH2), 3.64 (t, J=4.6 Hz, 4H, piperazine N(CH2)2), 7.06 (d, J=9.0 Hz, 2H, phenyl H-3 & H-5), 7.39 (dd, J=7.6, 4.7 Hz, 1H, pyridine H-5), 7.78 (d, br, J=7.7 Hz, 1H, pyridine H-4), 8.03 (d, J=8.9 Hz, 2H, phenyl H-2 & H-6), 8.17 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.50 (dd, J=4.6, 1.5 Hz, 1H, pyridine H-6), 8.56 (d, J=1.4 Hz, 1H, pyridine H-2), 13.22 (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-5e65a971657b4f94bf7eb1f3eae3c404
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

Loading…