Trifluoroacetic acid → HCID 68585755, compound

HRID 17619Notes

Reaction equation

HRID 17619 reaction equation
C([CH:5]1[C:9]([C:10]2[C:18]3[O:17][C:16]([CH:19]4[CH2:21][CH2:20]4)=[N:15][C:14]=3[C:13]([C:22]#[N:23])=[C:12]([CH3:24])[C:11]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:8][CH2:7][N:6]1C(N)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH:19]1([C:16]2[O:17][C:18]3[C:14](=[C:13]([C:22]#[N:23])[C:12]([CH3:24])=[C:11]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:10]=3[C:9]3[CH2:5][NH:6][CH2:7][CH:8]=3)[N:15]=2)[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86630886tert-Butyl 3-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)-2,5-dihydro-1H-pyrrole-1-carboxamide

Product 1

HCID 68585755HCID 68585755, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)-2,5-dihydro-1H-pyrrole-1-carboxamide (I-327) (52.0 mg, 0.118 mmol) was dissolved in dichloromethane (4 ml), and with cooling with ice, trifluoroacetic acid (2 ml) was added, followed by stirring at room temperature for 2 hours. The reaction liquid was concentrated under reduced pressure, dissolved in chloroform, washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, and the residue obtained by concentration under reduced pressure was purified by preparative TLC (eluent, chloroform:methanol=10:1, v/v) and purified in slurry with isopropyl ether to obtain the entitled compound (26.0 mg, 62%) as a white solid.

Workup

  1. additionwas added
  2. customThe reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. dissolutiondissolved in chloroform
  5. washwashed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe insoluble matter was separated by filtration
  8. customthe residue obtained by concentration under reduced pressure
  9. customwas purified by preparative TLC (eluent, chloroform
  10. custommethanol=10:1, v/v) and purified in slurry with isopropyl ether

Sources & evidence

ORD record
ord-b99e1987d83b4defb928ddd0d9c613c6
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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