Trifluoroacetic acid → HCID 68585271, compound

HRID 17621Notes

Reaction equation

HRID 17621 reaction equation
[CH3:1][N:2]([CH2:4][C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](OC(C)(C)C)=O)[CH3:3].FC(F)(F)C(O)=O.C(N(CC)CC)C.[CH:31]1([C:34]2[O:35][C:36]3[C:37](=[C:39]([C:51]#[N:52])[C:40]([CH3:50])=[C:41]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)C=3F)[N:38]=2)[CH2:33][CH2:32]1>ClCCl>[CH:31]1([C:34]2[O:35][C:36]3[C:37](=[C:39]([C:51]#[N:52])[C:40]([CH3:50])=[C:41]([C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)[C:10]=3[N:6]3[CH2:7][CH2:8][CH2:9][C@H:5]3[CH2:4][N:2]([CH3:1])[CH3:3])[N:38]=2)[CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 510414282-Cyclopropyl-7-fluoro-5-methyl-6-phenylbenzoxazole-4-carbonitrileHCID 60017963tert-Butyl (2S)-2-[(dimethylamino)methyl]pyrrolidine-1-carboxylate

Product 1

HCID 68585271HCID 68585271, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (2S)-2-[(dimethylamino)methyl]pyrrolidine-1-carboxylate (I-328) (92.0 mg, 0.403 mmol) was dissolved in dichloromethane (1 ml), and at room temperature, trifluoroacetic acid (1 ml) was added, followed by stirring at room temperature for 1 hour. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in dimethyl sulfoxide (2 ml), then triethylamine (84.2 μl, 0.604 mmol) and 2-cyclopropyl-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-173) (118 mg, 0.403 mmol) was added, followed by stirring in an oil bath at 100° C. for 5 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, and washed with water and saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, the residue obtained by concentration was purified by preparative TLC (eluent, chloroform:methanol=10:1, v/v) to obtain the entitled compound (32.0 mg, 20%) as a colorless oily substance.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in dimethyl sulfoxide (2 ml)
  4. stirringby stirring in an oil bath at 100° C. for 5 hours
  5. customThe reaction liquid
  6. concentrationwas concentrated under reduced pressure
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. washwashed with water and saturated brine
  9. dry with materialAfter drying over anhydrous sodium sulfate
  10. customthe insoluble matter was separated by filtration
  11. customthe residue obtained by concentration
  12. customwas purified by preparative TLC (eluent, chloroform

Sources & evidence

ORD record
ord-b176013cb1df432c96d384edb8094606
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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