HCID 136146882, compound → HCID 136146885, compound

HRID 1718972Notes

Reaction equation

HRID 1718972 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[C:22](=[O:23])[C:21]([CH2:24][C:25]5[CH:30]=[CH:29][C:28]([C:31]6[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=6[C:37]6[NH:41][C:40](=[O:42])[O:39][N:38]=6)=[CH:27][CH:26]=5)=[C:20]([CH2:43][CH2:44][CH3:45])[N:19]=[C:18]4[CH2:46][CH3:47])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4]CC1>O1CCCC1.C(OCC)(=O)C>[CH2:46]([C:18]1[N:17]([C:14]2[CH:13]=[CH:12][C:11]([N:8]3[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]3)=[CH:16][CH:15]=2)[C:22](=[O:23])[C:21]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[C:37]3[NH:41][C:40](=[O:42])[O:39][N:38]=3)=[CH:27][CH:26]=2)=[C:20]([CH2:43][CH2:44][CH3:45])[N:19]=1)[CH3:47]

Participants

4

Reactant 1

HCID 136146882HCID 136146882, compound

Product 1

HCID 136146885HCID 136146885, compoundYield 107.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-[4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)phenyl]-2-ethyl-5-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-6-propylpyrimidin-4(3H)-one (0.45 g) in tetrahydrofuran (10 mL)-1 M hydrochloric acid (10 mL) was stirred at 60° C. for 2 days. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.45 g, 38%).

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9426e67b3cff4c399a70395550a3f2ca
Source dataset
uspto-grants-2010_09
Patent number
US07803940B2

Reaction notes

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