Sodium Dithionite → HCID 59726998, compound

HRID 1363138Notes

Reaction equation

HRID 1363138 reaction equation
[N:1]1([C:10]2[N:15]=[C:14]3[N:16]([CH2:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)C(=O)[NH:18][C:13]3=[CH:12][CH:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.N1(C2N=C3N(CC4C=NC=CC=4)C=NC3=CC=2)C2C=CC=CC=2N=C1.N1(C2N=C(NCC3C=NC=CC=3)C([N+]([O-])=O)=CC=2)C2C=CC=CC=2N=C1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>CS(C)=O.O.C(OCC)(=O)C>[N:1]1([C:10]2[N:15]=[C:14]([NH:16][CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[C:13]([NH2:18])=[CH:12][CH:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

8

Reactant 4

HCID 24489Sodium DithioniteHCID 11951572HCID 11951572, compoundHCID 59727052HCID 59727052, compoundHCID 59727099HCID 59727099, compound

Product 1

HCID 59726998HCID 59726998, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(1H-Benzo[d]imidazol-1-yl)-3-(pyridin-3-ylmethyl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (50) and 5-(1H-benzo[d]imidazol-1-yl)-3-(pyridin-3-ylmethyl)-3H-imidazo[4,5-b]pyridine (51). A solution of 6-(1H-benzo[d]imidazol-1-yl)-3-nitro-N-(pyridin-3-ylmethyl)pyridin-2-amine (48) (50 mg) in 1 mL of DMSO was treated with a solution of Na2S2O4 (300 mg) in 1 mL of water. The mixture was stirred for two hours and diluted with 50 mL of ethyl acetate. The mixture was washed three times with 50 mL aliquots of saturated sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo to provide the intermediate 6-(1H-benzo[d]imidazol-1-yl)-N2-(pyridin-3-ylmethyl)pyridine-2,3-diamine (49). Half of the intermediate was dissolved in methylene chloride (2 mL) and treated with 1,1′-carbonyldiimidazole (46 mg) at RT for 16 h. The resulting crude mixture was purified by preparative TLC (1000 microns, 5% MeOH/CH2Cl2) to provide 7.1 mg of 5-(1H-benzo[d]imidazol-1-yl)-3-(pyridin-3-ylmethyl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (50): 1H-NMR (CDCl3) δ 10.0 (br s, 1H), 8.9 (s, 1H), 8.6 (d, 1H), 8.5 (s, 1H), 7.9 (m, 2H), 7.8 (m, 1H), 7.6 (d, 1H), 7.4 (m, 2H), 7.4 (m, 1H), 7.3 (d, 1H), 5.2 (s, 2H). The other half of the reduced intermediate was dissolved in 1 mL of formic acid and heated in a microwave at 220° C. for 10 minutes. The mixture was concentrated in vacuo, diluted with methylene chloride, and washed with saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried with sodium sulfate, filtered, and concentrated in vacuo.

Workup

  1. washThe mixture was washed three times with 50 mL aliquots of saturated sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4152b35c734e43bb9ab68df12b16106f
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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