Sodium Dithionite → HCID 178527149, compound

HRID 416848Notes

Reaction equation

HRID 416848 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+].[O:67]=[S:68]1(=[O:82])[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][S:68](=[O:82])(=[O: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 435816154-(1,1-Dioxo-1lambda~6~,4-thiazinan-4-yl)benzaldehydeHCID 468687795-Bromo-3-nitro-4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)pyridin-2-amineHCID 178482685HCID 178482685, compound

Product 1

HCID 178527149HCID 178527149, compoundYield 32%

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 (30 mg, 0.076 mmol), DMF (0.15 mL), ethanol (0.85 mL), 1M Na2S2O4 (3 eq, 0.23 mmol, 0.23 mL) and 4-(1,1-dioxothiomorpholino)benzaldehyde (1.1 eq, 0.084 mmol, 20 mg). After 6 h, concentration in vacuo and purification by preparative tlc (CH2Cl2-MeOH, 95:5) gave the product (14 mg, 32%) as a colourless solid; δH (500 MHz, DMSO-d6) 2.61 (s, br, 4H, piperazine N(CH2)2), 3.14 (t, J=4.7 Hz, 4H, 1,1-dioxothiomorpholine N(CH2)2), 3.61 (s, 2H, NCH2), 3.65 (t, J=4.6 Hz, 4H, piperazine N(CH2)2), 3.91 (t, J=5.0 Hz, 4H, 1,1-dioxothiomorpholine S(CH2)2), 7.16 (d, J=9.0 Hz, 2H, phenyl H-2 & H-6), 7.39 (dd, J=7.5, 4.8 Hz, 1H, pyridine H-5), 7.78 (dt, J=7.8, 1.9 Hz, 1H, pyridine H-4), 8.06 (d, J=9.0 Hz, 2H, phenyl H-3 & H-5), 8.18 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.49 (dd, J=4.7, 1.8 Hz, 1H, pyridine H-6), 8.56 (d, J=1.6 Hz, 1H, pyridine H-2), 13.26 (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-7e3ffef309ab4d12a1f70182e20eba72
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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