HCID 19369682, compound → HCID 19369587, compound

HRID 849232Notes

Reaction equation

HRID 849232 reaction equation
C(OC([N:8]([C:24]1[CH:29]=[C:28]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[CH:27]=[C:26]([CH2:36][S:37][C:38]2[S:39][C:40]([CH2:43][CH3:44])=[N:41][N:42]=2)[N:25]=1)[CH2:9][C:10]1[CH:15]=[C:14]([NH:16][C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[CH:13]=[C:12]([CH3:23])[CH:11]=1)=O)(C)(C)C>FC(F)(F)C(O)=O>[CH2:43]([C:40]1[S:39][C:38]([S:37][CH2:36][C:26]2[N:25]=[C:24]([NH:8][CH2:9][C:10]3[CH:15]=[C:14]([NH:16][C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[CH:13]=[C:12]([CH3:23])[CH:11]=3)[CH:29]=[C:28]([N:30]3[CH2:31][CH2:32][O:33][CH2:34][CH2:35]3)[CH:27]=2)=[N:42][N:41]=1)[CH3:44]

Participants

3

Reactant 1

HCID 19369682HCID 19369682, compound

Product 1

HCID 19369587HCID 19369587, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-{N-tert-butoxycarbonyl-N-[3-methyl-5-(2-propenyloxycarbonylamino)benzyl]amino}-6-(5-ethyl-1,3,4-thiadiazol-2-ylthiomethyl)-4-morpholinopyridine (92 mg) was dissolved in trifluoroacetic acid (1 ml), followed by stirring at room temperature for one hour. The reaction solution was concentrated under reduced pressure, and the residue was subjected to liquid separation with ethyl acetate-a saturated sodium hydrogen carbonate aqueous solution. The organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=50/1) to obtain the above identified compound (55 mg) as a pale yellow solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was subjected to liquid separation with ethyl acetate-a saturated sodium hydrogen carbonate aqueous solution
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform/methanol=50/1)
  7. customto obtain the

Sources & evidence

ORD record
ord-61201c90348b4d938a384916eedffa30
Source dataset
uspto-grants-2000_01
Patent number
US06011039

Reaction notes

Loading…