Sodium Dithionite → HCID 59727080, compound

HRID 1363147Notes

Reaction equation

HRID 1363147 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N+:35]([O-])=O)=[C:7]([NH:9][C:10]2[N:15]=[C:14]3[N:16]([C@@H:27]([C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)[CH3:28])[C:17](=[O:26])[N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:13]3=[CH:12][CH:11]=2)[CH:8]=1)#[N:2].[O-]S(S([O-])=O)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C1COCC1.O.C(OCC)(=O)C>[NH2:35][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][C:7]=1[NH:9][C:10]1[N:15]=[C:14]2[N:16]([C@@H:27]([C:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)[CH3:28])[C:17](=[O:26])[N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[C:13]2=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 59727072HCID 59727072, compound

Product 1

HCID 59727080HCID 59727080, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (R)-tert-butyl 5-(5-cyano-2-nitrophenylamino)-2-oxo-3-(1-(pyridin-3-yl)ethyl)-2,3-dihydroimidazo[4,5-b]pyridine-1-carboxylate (70) (100 mg) in THF (5 mL) was treated with an aqueous solution comprised of 0.5 g of Na2S2O4 and 0.25 g NaHCO3 in 5 mL of water. The mixture went quickly from a red color to a slightly yellow color, which indicated reduction of the nitro group. The mixture was diluted with ethyl acetate and washed with saturated sodium chloride solution. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated to provide the intermediate (R)-tert-butyl 5-(2-amino-5-cyanophenylamino)-2-oxo-3-(1-(pyridin-3-yl)ethyl)-2,3-dihydroimidazo[4,5-b]pyridine-1-carboxylate (71). The intermediate was dissolved in THF (5 mL), DMF (1 mL), and trimethylorthoformate (2 mL). The mixture was treated with 10 mg of p-toluenesulfonic acid and stirred for 20 h. The mixture was diluted with ethyl acetate and washed once with saturated sodium bicarbonate and twice with saturated NaCl solution. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated. Column chromatography (2% MeOH in methylene chloride) provided 57 mg tert-Butyl 5-(6-cyano-1H-benzo[d]imidazol-1-yl)-2-oxo-3-((R)-1-(pyridin-3-yl)ethyl)-2,3-dihydroimidazo[4,5-b]pyridine-1-carboxylate (72).

Workup

  1. washwashed with saturated sodium chloride solution
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fff41f9847cc46f881b7b94e0b67b5f2
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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