Ethyl Acetate → HCID 9795266, compound

HRID 549029Notes

Reaction equation

HRID 549029 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:21][C:16]3=[N:17][CH:18]=[CH:19][N:20]=[C:15]3[CH:14]=2)=[CH:9][CH:8]=1)(=O)=O.O1CCOCC1.[NH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1.C(OCC)(=O)C>CO>[N:30]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[NH:21][C:16]4=[N:17][CH:18]=[CH:19][N:20]=[C:15]4[CH:14]=3)=[CH:9][CH:8]=2)[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 31268PyrrolidineHCID 312751,4-DioxaneHCID 22477192HCID 22477192, compound

Product 1

HCID 9795266HCID 9795266, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 6-(4-trifluoromethanesulfonyloxyphenyl)-5H-pyrrolo[2,3-b]pyrazine [20 mg, Reference Example 18(e)], dioxane (3 mL) and pyrrolidine (0.2 mL) was heated at 200° C. in a microwave oven for 1 hour. The reaction mixture was then evaporated and the residue was subjected to chromatography on silica eluting with a mixture of ethyl acetate and heptane (1:1, v/v) to give, after trituration with a mixture of ethyl acetate and methanol, the title compound (11 mg) as a yellow solid. MS: 265.1 (MH+). RT=2.92 minutes.

Workup

  1. customThe reaction mixture was then evaporated
  2. additionthe residue was subjected to chromatography on silica eluting with a mixture of ethyl acetate and heptane (1:1
  3. customv/v) to give

Sources & evidence

ORD record
ord-92aecc8ec25341489dd08031a27d6c27
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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