Trifluoroacetic acid → HCID 53385937, compound

HRID 1898544Notes

Reaction equation

HRID 1898544 reaction equation
[CH3:1][CH:2]([CH3:38])[C@@H:3]([NH:11][C:12]([C:14]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:21]=2)[N:16](COCC[Si](C)(C)C)[CH:15]=1)=[O:13])[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].FC(F)(F)C(O)=O>ClCCl>[CH3:1][CH:2]([CH3:38])[C@@H:3]([NH:11][C:12]([C:14]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]([O:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:21]=2)[NH:16][CH:15]=1)=[O:13])[C:4]([N:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1)=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67386157HCID 67386157, compound

Product 1

HCID 53385937HCID 53385937, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-phenoxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-methyl-1-(pyrrolidine-1-carbonyl)-propyl]-amide from Step 3 in dichloromethane (0.5 mL) was added trifluoroacetic acid (0.7 mL). The reaction mixture was stirred at room temperature overnight then concentrated. The residue was stirred with THF (1 mL), water (0.5 mL), and Et3N (0.5 mL) for 2 h then concentrated. The residue was partitioned between ethyl acetate and water and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and concentrated. The residue was purified by SiO2 column chromatography (5% MeOH/CH2Cl2) to provide 0.049 g (46%, 2 steps) of 2-phenoxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-methyl-1-(pyrrolidine-1-carbonyl)-propyl]-amide as a white foam. MS: 408 (M+H)+.

Workup

  1. concentrationthen concentrated
  2. stirringThe residue was stirred with THF (1 mL), water (0.5 mL), and Et3N (0.5 mL) for 2 h
  3. concentrationthen concentrated
  4. customThe residue was partitioned between ethyl acetate and water
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by SiO2 column chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f21d81cfe7b34f218862f9a192dc3b0c
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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