Sodium Dithionite → HCID 178508032, compound

HRID 1363205Notes

Reaction equation

HRID 1363205 reaction equation
[N:1]1([C:10]2[N:15]=[C:14]([NH:16][C@H:17]3[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]3)[C:13]([N+:24]([O-])=O)=[CH:12][N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C1COCC1.O.CCOC(C)=O>[NH2:24][C:13]1[C:14]([NH:16][C@H:17]2[CH2:18][CH2:19][C@H:20]([OH:23])[CH2:21][CH2:22]2)=[N:15][C:10]([N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[CH:2]2)=[N:11][CH:12]=1

Participants

7

Reactant 3

HCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 178526814HCID 178526814, compound

Product 1

HCID 178508032HCID 178508032, compoundYield 101.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of trans-4-(2-(1H-benzo[d]imidazol-1-yl)-5-nitropyrimidin-4-ylamino)cyclohexanol (162 mg) in THF (20 ml) was treated with a solution of sodium hydrosulfite (500 mg) and NaHCO3 (500 mg) in 20 mL of water and stirred for 25 minutes. The mixture was diluted with 200 mL EtOAc and washed twice with saturated sodium chloride. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo to provide 150 mg of the title compound.

Workup

  1. washwashed twice with saturated sodium chloride
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-84ae3b885bb741ec88ae99834fdb4917
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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