HCID 19369594, compound → HCID 19369622, compound

HRID 849233Notes

Reaction equation

HRID 849233 reaction equation
C(OC([N:8]([C:31]1[CH:36]=[C:35]([N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)[CH:34]=[C:33]([CH2:43][S:44][C:45]2[S:46][C:47]([CH2:50][CH3:51])=[N:48][N:49]=2)[N:32]=1)[CH2:9][C:10]1[CH:15]=[C:14]([CH2:16][O:17]C2CCCCO2)[CH:13]=[C:12]([NH:24][C:25]([O:27][CH2:28][CH:29]=[CH2:30])=[O:26])[CH:11]=1)=O)(C)(C)C>Cl.CO.C(OCC)(=O)C>[CH2:50]([C:47]1[S:46][C:45]([S:44][CH2:43][C:33]2[N:32]=[C:31]([NH:8][CH2:9][C:10]3[CH:11]=[C:12]([NH:24][C:25]([O:27][CH2:28][CH:29]=[CH2:30])=[O:26])[CH:13]=[C:14]([CH2:16][OH:17])[CH:15]=3)[CH:36]=[C:35]([N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)[CH:34]=2)=[N:49][N:48]=1)[CH3:51]

Participants

4

Reactant 1

HCID 19369594HCID 19369594, compound

Product 1

HCID 19369622HCID 19369622, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21893726Hydrochloride methanolSolvent

Conditions

Temperature
60 °C

Procedure

2-{N-tert-butoxycarbonyl-N-[3-(2-propenyloxycarbonylamino)-5-(2-tetrahydropyranyl)oxymethylbenzyl]amino}-6-(5-ethyl-1,3,4-thiadiazol-2-ylthiomethyl)-4-morpholinopyridine (51 mg) was dissolved in 10% hydrogen chloride-methanol (2 ml), followed by stirring at 60° C. for two hours. After cooling naturally, the reaction solution was diluted with ethyl acetate, washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution and then, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by thin layer chromatography for separation (chloroform/methanol=10/1) to obtain the above identified compound (55 mg) as a pale yellow amorphous solid.

Workup

  1. temperatureAfter cooling naturally
  2. washwashed with a saturated sodium hydrogen carbonate aqueous solution
  3. dry with materiala saturated sodium chloride aqueous solution and then, dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by thin layer chromatography for separation (chloroform/methanol=10/1)
  6. customto obtain the

Sources & evidence

ORD record
ord-0ecedf044906468fa48307901beb8ec6
Source dataset
uspto-grants-2000_01
Patent number
US06011039

Reaction notes

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