Ethanol → HCID 178507655, compound

HRID 600454Notes

Reaction equation

HRID 600454 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([NH:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[N+:19]([O-])=O)[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:29])[N:6]2[C@H:22]1[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]1.O.CCO.[NH4+].[OH-]>CC(O)=O.CCOC(C)=O.[Fe]>[NH2:19][C:13]1[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:12]=1[NH:11][C:9]1[N:8]=[C:7]2[C:3]([NH:4][C:5](=[O:29])[N:6]2[C@H:22]2[CH2:23][CH2:24][C@H:25]([OH:28])[CH2:26][CH2:27]2)=[C:2]([Cl:1])[N:10]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14923Ammonium HydroxideHCID 178518647HCID 178518647, compound

Product 1

HCID 178507655HCID 178507655, compoundYield 101.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

6-chloro-2-(5-fluoro-2-nitrophenylamino)-9-(trans-4-hydroxycyclohexyl)-7H-purin-8(9H)-one (13.5 mg, 0.03 mmol) was dissolved in CH3COOH:H2O:EtOH (1 mL:2.5 mL:5 mL) and iron powder (18 mg, 0.32 mmol, 10 equiv.) was added. The reaction mixture was then heated to 90° C. with continuous stirring for 15 minutes. Completion of the reaction was monitored by analytical HPLC and MS analysis. The reaction mixture was cooled to room temperature. Saturated NH4OH was added to the cooled solution slowly, with stirring, until pH was 11-12. It was then diluted with EtOAc (15 mL). The organic layer was separated, and the aqueous layer extracted with EtOAc (3×15 mL), the combined organic layers were washed with brine (1×15 mL), dried over MgSO4 and concentrated to give a white solid (12 mg, 96% yield), which was used without purification in the next step. MS (EI) m/z 393 (MH)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringwith stirring, until pH was 11-12
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with EtOAc (3×15 mL)
  5. washthe combined organic layers were washed with brine (1×15 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-07d25744390f4750aef301f51e802e27
Source dataset
uspto-grants-2011_03
Patent number
US07902187B2

Reaction notes

Loading…