Trifluoroacetic acid → HCID 54755742, compound

HRID 2191573Notes

Reaction equation

HRID 2191573 reaction equation
[CH:1]1([NH:7][C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([CH:19]4[CH2:21][CH2:20]4)[N:17]=3)[N:12](COCC[Si](C)(C)C)[CH:11]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:1]1([NH:7][C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([CH:19]4[CH2:21][CH2:20]4)[N:17]=3)[NH:12][CH:11]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67002026HCID 67002026, compound

Product 1

HCID 54755742HCID 54755742, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 10 mL round-bottomed flask, 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid cyclohexylamide (94 mg, 0.23 mmol) was dissolved in CH2Cl2 (0.9 mL). Trifluoroacetic acid (0.7 mL) was added and the light yellow reaction mixture was stirred at room temperature for 2 h then concentrated. The residue was taken up in toluene (3 mL), concentrated and then dried under high vacuum. The residue was dissolved in CH2Cl2 (0.9 mL) and ethylenediamine (0.9 mL) was added. The reaction mixture was stirred at room temperature for 2 h then H2O and EtOAc were added. The resultant suspension was filtered, rinsing with H2O and EtOAc and dried under high vacuum to afford 55 mg (85%) of 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid cyclohexylamide as a white solid. MS: (M+H)+=285; mp>300.0.

Workup

  1. concentrationthen concentrated
  2. concentrationconcentrated
  3. customdried under high vacuum
  4. dissolutionThe residue was dissolved in CH2Cl2 (0.9 mL)
  5. additionethylenediamine (0.9 mL) was added
  6. stirringThe reaction mixture was stirred at room temperature for 2 h
  7. additionH2O and EtOAc were added
  8. filtrationThe resultant suspension was filtered
  9. washrinsing with H2O and EtOAc
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-e472dc5737604ad596bbbd34e2ed52f2
Source dataset
uspto-grants-2012_12
Patent number
US08329699B2

Reaction notes

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