Trifluoroacetic acid → HCID 53389792, compound

HRID 446933Notes

Reaction equation

HRID 446933 reaction equation
[CH2:1]([NH:3][C:4]([CH2:6][CH:7]([NH:9][C:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([CH:21]3[CH2:23][CH2:22]3)[N:19]=2)[N:14](COCC[Si](C)(C)C)[CH:13]=1)=[O:11])[CH3:8])=[O:5])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([NH:3][C:4]([CH2:6][CH:7]([NH:9][C:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([CH:21]3[CH2:22][CH2:23]3)[N:19]=2)[NH:14][CH:13]=1)=[O:11])[CH3:8])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67388110HCID 67388110, compound

Product 1

HCID 53389792HCID 53389792, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-ethylcarbamoyl-1-methyl-ethyl)-amide (0.114 g, 0.25 mmol) in CH2Cl2 (8 mL) was added trifluoroacetic acid (1.0 mL). The reaction mixture was stirred at room temperature overnight then concentrated. The residue was dissolved in MeOH (7 mL) and H2O (0.5 mL) and Et3N (1 mL) were added. The reaction mixture was stirred at room temperature overnight then concentrated. The residue was purified by SiO2 chromatography (4% MeOH/CH2Cl2) to afford 0.012 g (16%) of 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-ethylcarbamoyl-1-methyl-ethyl)-amide as a white solid. MS: (M+H)+=316; mp=182.0-184.0.

Workup

  1. concentrationthen concentrated
  2. dissolutionThe residue was dissolved in MeOH (7 mL)
  3. additionH2O (0.5 mL) and Et3N (1 mL) were added
  4. stirringThe reaction mixture was stirred at room temperature overnight
  5. concentrationthen concentrated
  6. customThe residue was purified by SiO2 chromatography (4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f63084b3cc594e0cbdc46d394f399186
Source dataset
uspto-grants-2013_07
Patent number
US08481541B2

Reaction notes

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