Trifluoroacetic acid → HCID 54755625, compound

HRID 2191564Notes

Reaction equation

HRID 2191564 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C:10]([NH:17][C:18]([C:20]2[C:28]3[C:23](=[N:24][CH:25]=[C:26]([CH:29]4[CH2:31][CH2:30]4)[N:27]=3)[N:22](COCC[Si](C)(C)C)[CH:21]=2)=[O:19])([C:13]([OH:16])([CH3:15])[CH3:14])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[OH:16][C:13]([C:10]1([NH:17][C:18]([C:20]2[C:28]3[C:23](=[N:24][CH:25]=[C:26]([CH:29]4[CH2:30][CH2:31]4)[N:27]=3)[NH:22][CH:21]=2)=[O:19])[CH2:11][CH2:12][NH:8][CH2:9]1)([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67002437HCID 67002437, compound

Product 1

HCID 54755625HCID 54755625, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 10 mL round-bottomed flask, 3-{[2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbonyl]-amino}-3-(1-hydroxy-1-methyl-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (118 mg, 0.21 mmol) was dissolved in CH2Cl2 (1 mL). Trifluoroacetic acid (0.8 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 (1 mL) and ethylenediamine (1 mL) was added. The reaction mixture was stirred at room temperature for 1 h then H2O and EtOAc were added. The aqueous layer was extracted with EtOAc. The combined organics were washed with H2O and brine, dried over Na2SO4 and concentrated. The residue was triturated with EtOAc to afford 37 mg (48%) of 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [3-(1-hydroxy-1-methyl-ethyl)-pyrrolidin-3-yl]-amide as a yellow solid.

Workup

  1. concentrationthen concentrated
  2. concentrationconcentrated
  3. customdried under high vacuum
  4. dissolutionThe residue was dissolved in CH2Cl2 (1 mL)
  5. additionethylenediamine (1 mL) was added
  6. stirringThe reaction mixture was stirred at room temperature for 1 h
  7. additionH2O and EtOAc were added
  8. extractionThe aqueous layer was extracted with EtOAc
  9. washThe combined organics were washed with H2O and brine
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated
  12. customThe residue was triturated with EtOAc

Sources & evidence

ORD record
ord-cc87b0bda3a2451bb23b61a333f947c0
Source dataset
uspto-grants-2012_12
Patent number
US08329699B2

Reaction notes

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