Sodium Dithionite → HCID 178480649, compound

HRID 416834Notes

Reaction equation

HRID 416834 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+].[CH3:67][N:68]1[CH2:73][CH2:72][N:71]([C:74]2[CH:81]=[CH:80][C:77]([CH:78]=O)=[CH:76][CH:75]=2)[CH2:70][CH2:69]1>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:78]([C:77]3[CH:76]=[CH:75][C:74]([N:71]4[CH2:70][CH2:69][N:68]([CH3:67])[CH2:73][CH2:72]4)=[CH:81][CH:80]=3)[NH:42][C:39]2=[N:40][CH:41]=1

Participants

7

Reactant 4

HCID 24489Sodium DithioniteHCID 7365334-(4-Methylpiperazin-1-yl)benzaldehydeHCID 468687795-Bromo-3-nitro-4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)pyridin-2-amineHCID 178482685HCID 178482685, compound

Product 1

HCID 178480649HCID 178480649, compoundYield 39.4%

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-phenyl piperazine-1-carboxamide, but here using 5-bromo-3-nitro-4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)pyridin-2-amine (20 mg, 0.051 mmol), DMF (0.15 mL), ethanol (0.85 mL), 1M Na2S2O4 (3 eq, 0.15 mmol, 0.15 mL) and 4-(4-methylpiperazino)benzaldehyde (1.1 eq, 0.056 mmol, 11 mg). After 6 h, concentration in vacuo and purification by preparative tlc (CH2Cl2-MeOH, 9:1) gave the product (11 mg, 39%) as a colourless solid; δH (500 MHz, DMSO-d6) 2.26 (s, 3H, CH3), 2.49 (s, br, 4H, piperazine N(CH2)2), 2.63 (s, br, 4H, piperazine N(CH2)2), 3.30 (hidden by DMSO peak, 4H, piperazine N(CH2)2), 3.62 (s, 2H, NCH2), 3.65 (t, J=4.2 Hz, 4H, piperazine N(CH2)2), 7.06 (d, J=8.7 Hz, 2H, phenyl H-3 & H-5), 7.40 (dd, J=7.7, 4.8 Hz, 1H, pyridine H-5), 7.79 (d, br, J=7.7 Hz, 1H, pyridine H-4), 8.03 (d, J=8.7 Hz, 2H, phenyl H-2 & H-6), 8.18 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.50 (d, J=4.5 Hz, 1H, pyridine H-6), 8.57 (s, br, 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, 9:1)

Sources & evidence

ORD record
ord-fe706421943944ecb41d9e0391067a9d
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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