HCID 19369665, compound → HCID 19369747, compound

HRID 849235Notes

Reaction equation

HRID 849235 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][CH2:37][C:38]2[S:39][C:40]([CH2:44][CH3:45])=[C:41]([CH3:43])[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]([Cl:23])[CH:11]=1)=O)(C)(C)C>FC(F)(F)C(O)=O>[Cl:23][C:12]1[CH:11]=[C:10]([CH:15]=[C:14]([NH:16][C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[CH:13]=1)[CH2:9][NH: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][CH2:37][C:38]2[S:39][C:40]([CH2:44][CH3:45])=[C:41]([CH3:43])[N:42]=2)[N:25]=1

Participants

3

Reactant 1

HCID 19369665HCID 19369665, compound

Product 1

HCID 19369747HCID 19369747, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-{N-tert-butoxycarbonyl-N-[3-chloro-5-(2-propenyloxycarbonylamino)benzyl]amino}-6-[2-(5-ethyl-4-methyl-1,3-thiazol-2-yl)ethyl]-4-morpholinopyridine (470 mg) was dissolved in trifluoroacetic acid (5 ml), followed by stirring at room temperature for 30 minutes. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate, washed with a saturated sodium hydrogen carbonate aqueous solution and 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→20/1) to obtain the above identified compound (307 mg) as a white solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with a saturated sodium hydrogen carbonate aqueous solution
  4. dry with materiala saturated sodium chloride aqueous solution and then, dried 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→20/1)
  7. customto obtain the

Sources & evidence

ORD record
ord-86f645737b244d9b89179b502babf457
Source dataset
uspto-grants-2000_01
Patent number
US06011039

Reaction notes

Loading…