Sodium Chloride → HCID 178452759, compound

HRID 1363209Notes

Reaction equation

HRID 1363209 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([NH:16][C:17]2[N:22]=[C:21]([NH:23][C@H:24]3[CH2:29][CH2:28][C@H:27]([OH:30])[CH2:26][CH2:25]3)[C:20]([N+:31]([O-])=O)=[CH:19][N:18]=2)[CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C1COCC1>[NH2:31][C:20]1[C:21]([NH:23][C@H:24]2[CH2:25][CH2:26][C@H:27]([OH:30])[CH2:28][CH2:29]2)=[N:22][C:17]([NH:16][C:4]2[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=2[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:18][CH:19]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 178452760HCID 178452760, compound

Product 1

HCID 178452759HCID 178452759, compoundYield 107.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 4-fluoro-2-(4-(trans-4-hydroxycyclohexylamino)-5-nitropyrimidin-2-ylamino)phenylcarbamate (110 mg) in THF (30 mL) was treated with a mixture containing sodium hydrosulfite (600 mg in 20 ml H2O) and sodium bicarbonate (10 ml, saturated). The resulting mixture was stirred for 5 minutes during which the color changed from yellow to almost colorless. Saturated sodium chloride was added and the mixture was extracted with EtOAc twice. The combined organic layers were washed with saturated sodium chloride and separated. The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo to provide 111 mg of the title compound.

Workup

  1. extractionthe mixture was extracted with EtOAc twice
  2. washThe combined organic layers were washed with saturated sodium chloride
  3. customseparated
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac331f48da4e4e4189029f907449e373
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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