Hexane → HCID 67345923, compound

HRID 1677404Notes

Reaction equation

HRID 1677404 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]([O:43][C:44]([N:46]1[CH2:50][CH2:49][CH:48]([C:51](=[O:56])N(OC)C)[CH2:47]1)=[O:45])([CH3:42])([CH3:41])[CH3:40]>C1COCC1>[C:39]([O:43][C:44]([N:46]1[CH2:50][CH2:49][CH:48]([C:51]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:11]4[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=4)[N:9]=3)[NH:4][CH:3]=2)=[O:56])[CH2:47]1)=[O:45])([CH3:42])([CH3:41])[CH3:40]

Participants

5

Reactant 3

HCID 8058HexaneHCID 57419605Tert-butyl 3-[methoxy(methyl)carbamoyl]pyrrolidine-1-carboxylateHCID 595405257-iodo-5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 67345923HCID 67345923, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 0.061 ml of 2.13M Buli in hexane solution (0.13 mM, 1.3 eq) was added and the now yellow mixture was stirred for 30 seconds then 3-(Methoxy-methyl-carbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester, 0.052 gm, 0.2 mM, 2 eq.) in a minimal amount of THF was added by syringe. The mixture was stirred for 30 minutes, removed from the dry ice-acetone bath and immediately quenched with a saturated aqueous ammonium chloride solution. The mixture was extracted two times with ethyl acetate and the organic extracts dried over magnesium sulfate. After filtering and concentrating, the oil was redissolved in THF and 0.2 ml of 1M Tetrabutylammonium Fluoride in THF added. After 5 minutes the mixture was concentrated and purified on a preparative thin-layer chromatography plate (Ethylacetate/hexane) to give 3-[2-(3,4,5-Trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-pyrrolidine-1-carboxylic acid tert-butyl ester. The 3-[2-(3,4,5-Trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-pyrrolidine-1-carboxylic acid tert-butyl ester was dissolved in 3 ml of dichloromethane and 0.4 ml trifluoroacetic acid was added and stirred overnight. The solution was concentrated and the solid dried overnight at 2 torr in a 60° C. vacuum oven to give 0.012 gm of Pyrrolidin-3-yl-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone trifluoroacetate salt. (M+H)+=383.

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 a saturated aqueous ammonium chloride solution
  9. extractionThe mixture was extracted two times with ethyl acetate
  10. dry with materialthe organic extracts dried over magnesium sulfate
  11. filtrationAfter filtering
  12. concentrationconcentrating
  13. dissolutionthe oil was redissolved in THF
  14. addition0.2 ml of 1M Tetrabutylammonium Fluoride in THF added
  15. concentrationAfter 5 minutes the mixture was concentrated
  16. custompurified on a preparative thin-layer chromatography plate (Ethylacetate/hexane)

Sources & evidence

ORD record
ord-c224b80c7940482caa26071cb4ab75b7
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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