Methanol → HCID 59727131, compound

HRID 1363144Notes

Reaction equation

HRID 1363144 reaction equation
[CH3:1][O:2][C:3]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:4]=1[CH2:5][N:6]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([NH:23][C@@H:24]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH3:25])[N:15]=1)[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[O-]S(S([O-])=O)=O.[Na+].[Na+].C([O-])(O)=O.[Na+].CO>C1COCC1.O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:4]=1[CH2:5][N:6]([C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([NH:23][C@@H:24]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH3:25])[N:15]=1)[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:10])[CH3:11]

Participants

8

Reactant 4

HCID 887MethanolHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 59726978HCID 59726978, compound

Product 1

HCID 59727131HCID 59727131, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (R)-tert-butyl 2,4-dimethoxybenzyl(5-nitro-6-(1-(pyridin-3-yl)ethylamino)pyridin-2-yl)carbamate (500 mg) in THF (25 mL) was treated with an aqueous solution comprised of 2 g of Na2S2O4 and 1 g NaHCO3 in 20 mL of water followed by 1 mL of methanol. The mixture was stirred for 30 minutes, then 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 2,4-dimethoxybenzyl(5-amino-6-(1-(pyridin-3-yl)ethylamino)pyridin-2-yl)carbamate (66). The intermediate was dissolved in THF (50 mL) and treated with 1,1′-carbonyldiimidazole (0.5 g) at 50° C. for 20 h. The mixture was concentrated and purified by column chromatography (2→5% MeOH in methylene chloride) to provide 413 mg of (R)-tert-Butyl 2,4-dimethoxybenzyl(2-oxo-3-(1-(pyridin-3-yl)ethyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)carbamate (67).

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-3058dc1a52444be4867b9482ed5bddb5
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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