Trifluoroacetic acid → HCID 66775076, compound

HRID 255387Notes

Reaction equation

HRID 255387 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[CH:8][C:9](=[O:30])[N:10]2[CH:13]([CH3:29])[CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([NH:21]C(=O)OC(C)(C)C)[CH2:17][CH2:16]2)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:21][CH:18]1[CH2:19][CH2:20][N:15]([CH2:14][CH:13]([N:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[N:7]=[CH:8][C:9]2=[O:30])[CH3:29])[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86642667HCID 86642667, compound2×

Product 1

HCID 66775076HCID 66775076, compoundYield 105.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl {1-[2-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)propyl]piperidin-4-yl}carbamate (Intermediate 222, 200 mg, 0.48 mmol) in dichloromethane (30 mL) was treated with trifluoroacetic acid (3 mL). After 2 hours, the reaction was concentrated to dryness. The residue was partitioned between 15% methanol/chloroform. The aqueous phase was re-extracted 3× with 15% methanol/chloroform. The combined organic phases were dried over magnesium sulfate, filtered, and concentrated to dryness giving 160 mg (100%) of the crude product as an oil.

Workup

  1. concentrationthe reaction was concentrated to dryness
  2. customThe residue was partitioned between 15% methanol/chloroform
  3. extractionThe aqueous phase was re-extracted 3× with 15% methanol/chloroform
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ecb20ee5bf2c4ddfb9bd80f4c1be3d9c
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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