Phenyl isocyanate → HCID 44206943, compound

HRID 1677407Notes

Reaction equation

HRID 1677407 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=3)[N:9]=2)[N:4]([Si](C(C)C)(C(C)C)C(C)C)[CH:3]=1.CCCCCC.[C:39]1([N:45]=[C:46]=[O:47])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>>[C:39]1([NH:45][C:46]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:11]4[CH:12]=[C:13]([O:21][CH3:22])[C:14]([O:19][CH3:20])=[C:15]([O:17][CH3:18])[CH:16]=4)[N:9]=3)[NH:4][CH:3]=2)=[O:47])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

4

Reactant 3

HCID 7672Phenyl isocyanateHCID 8058HexaneHCID 595405257-iodo-5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 44206943HCID 44206943, compound

Procedure

7-Iodo-5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine 0.057 gm, 0.1 mM was placed in an oven dried flask and 1 ml anhydrous THF was added. The flask was chilled in an Acetone-dry ice slurry and evacuated and refilled 3 times with nitrogen. Via syringe 0.065 ml of 2.13M Buli in hexane solution (0.14 mM, 1.4 eq) was added and the now yellow mixture was stirred for 30 seconds then phenylisocyanate, 0.027 ml, 0.25 mM, 2.5 eq.) was added. The mixture was stirred for 30 minutes, removed from the dry ice-acetone bath and immediately quenched with saturated aqueous ammonium chloride. Ethyl acetate was added and insoluble material removed by filtration and discarded. The mixture was separated and the aqueous layer was extracted two times with ethyl acetate. The organic layers were rinsed three times with 0.1M HCl and dried over magnesium sulfate. The solution was concentrated and purified on a silica gel column (ethyl acetate/hexane gradient). The product was recrystallized from acetonitrile and dried at 2 torr in a 60° C. vacuum oven overnight to give 2-(3,4,5-Trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid phenylamide. (M+H)+=405.

Workup

  1. customdried flask
  2. addition1 ml anhydrous THF was added
  3. temperatureThe flask was chilled in an Acetone-dry ice slurry
  4. customevacuated
  5. additionrefilled 3 times with nitrogen
  6. stirringThe mixture was stirred for 30 minutes
  7. customremoved from the dry ice-acetone bath
  8. customimmediately quenched with saturated aqueous ammonium chloride
  9. additionEthyl acetate was added
  10. custominsoluble material removed by filtration
  11. customThe mixture was separated
  12. extractionthe aqueous layer was extracted two times with ethyl acetate
  13. washThe organic layers were rinsed three times with 0.1M HCl
  14. dry with materialdried over magnesium sulfate
  15. concentrationThe solution was concentrated
  16. custompurified on a silica gel column (ethyl acetate/hexane gradient)
  17. customThe product was recrystallized from acetonitrile
  18. customdried at 2 torr in a 60° C. vacuum oven overnight

Sources & evidence

ORD record
ord-13fc30c40db54254947a40094f34bc10
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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