Sodium Dithionite → HCID 178453344, compound

HRID 416831Notes

Reaction equation

HRID 416831 reaction equation
BrC1N(C(NC2C=CC=CC=2)=O)C(C2C=CN=C3NC(C4C=CC(N(C)C)=CC=4)=NC=23)CNC1.[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=[CH:68][CH2:69][CH2:70][NH:71][C:72](=[O:78])[O:73][C:74]([CH3:77])([CH3:76])[CH3:75]>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:68]([CH2:69][CH2:70][NH:71][C:72](=[O:78])[O:73][C:74]([CH3:77])([CH3:76])[CH3:75])[NH:42][C:39]2=[N:40][CH:41]=1

Participants

7

Reactant 4

HCID 24489Sodium DithioniteHCID 10910051tert-Butyl N-(3-oxopropyl)carbamateHCID 468687795-Bromo-3-nitro-4-(4-(pyridin-3-ylmethyl)piperazin-1-yl)pyridin-2-amineHCID 1784826576-bromo-2-(4-(dimethylamino)phenyl-3H-imidazo[4,5-b]pyridin-7-yl)-N-phenylpiperazine-1-carboxamide

Product 1

HCID 178453344HCID 178453344, compoundYield 37%

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 (64 mg, 0.16 mmol), DMF (0.15 mL), ethanol (0.85 mL), 1M Na2S2O4 (3 eq, 0.49 mmol, 0.49 mL) and tert-butyl 3-oxopropylcarbamate (prepared according to the procedure described in Tetrahedron 2003, 59, 1719) (1.1 eq, 0.18 mmol, 31 mg). After 6 h, concentration in vacuo and purification by preparative tlc (CH2Cl2-MeOH, 9:1) gave the product (31 mg, 37%) as a colourless solid; δH (500 MHz, DMSO-d6) 1.35 (s, 9H, C(CH3)3), 2.58 (s, br, 4H, piperazine N(CH2)2), 2.89 (t, J=5.5 Hz, 2H, CH2CH2NH), 3.30 (hidden by DMSO peak, 2H, CH2CH2NH), 3.57 (t, J=4.4 Hz, 4H, piperazine N(CH2)2), 3.59 (s, 2H, NCH2Ar), 6.92 (s, br, 1H, NH), 7.38 (dd, J=7.7, 4.8 Hz, 1H, pyridine H-5), 7.76 (dt, J=7.7, 1.5 Hz, 1H, pyridine H-4), 8.16 (s, 1H, imidazo[4,5-b]pyridine H-5), 8.48 (dd, J=4.8, 1.5 Hz, 1H, pyridine H-6), 8.54 (d, J=1.5 Hz, 1H, pyridine H-2), 12.79 (s, br, 1H, imidazo[4,5-b]pyridine NH);

Workup

  1. customThis was prepared
  2. customprepared
  3. concentrationconcentration
  4. customin vacuo and purification by preparative tlc (CH2Cl2-MeOH, 9:1)

Sources & evidence

ORD record
ord-6a79bfa2409242ebb21b480f85524de7
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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