Hydrochloric Acid → HCID 59540736, compound

HRID 1677534Notes

Reaction equation

HRID 1677534 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([C:19]2[N:20]=[C:21]3[C:27]([C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:26][N:25](COCC[Si](C)(C)C)[C:22]3=[N:23][CH:24]=2)[CH:11]=[C:12]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:13]=1)(=[O:4])=[O:3].CO.Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O>[CH3:1][S:2]([CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([C:19]2[N:20]=[C:21]3[C:27]([C:28](=[O:33])[C:29]([CH3:31])([CH3:30])[CH3:32])=[CH:26][NH:25][C:22]3=[N:23][CH:24]=2)[CH:11]=[C:12]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:13]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 59540679HCID 59540679, compound

Product 1

HCID 59540736HCID 59540736, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a flask containing 1-[2-[3-(2-methanesulfonyl-ethoxy)-5-pyrrolidin-1-yl-phenyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (75 mg, 0.13 mmol) was added methanol (1 ml) and aqueous 6N HCl (1.5 ml). The flask was capped and placed in a heated oil bath (90° C.). After stirring for 50 minutes the mixture was cooled to ambient and the volatiles were stripped (rotovap/pump). The remainder was taken up in EtOAc (15 ml) and 5% aqueous NaHCO3 (15 ml) and stirred for 5 minutes. The material was partitioned and the organic phase collected and washed with brine (15 ml). The aqueous phases were back extracted with EtOAc (2×15 ml). The organics were combined, dried (MgSO4), filtered and stripped to provide a crude semi-solid. The material was purified by crystallization from hot CH2Cl2/hexanes (containing 4 drops of methanol) to afford 38 mg of 1-{2-[3-(2-methanesulfonyl-ethoxy)-5-pyrrolidin-1-yl-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one as a yellow solid. MP 230-232° C., M+H=471.

Workup

  1. customThe flask was capped
  2. customplaced in a heated oil bath
  3. custom(90° C.)
  4. temperaturewas cooled to ambient and the volatiles
  5. customThe material was partitioned
  6. customthe organic phase collected
  7. washwashed with brine (15 ml)
  8. extractionThe aqueous phases were back extracted with EtOAc (2×15 ml)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customto provide a crude semi-solid
  12. customThe material was purified by crystallization from hot CH2Cl2/hexanes (containing 4 drops of methanol)

Sources & evidence

ORD record
ord-ce0f72531eca41f6b80e587749db1cee
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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