HCID 136146882, compound → HCID 136146885, compound

HRID 1674302Notes

Reaction equation

HRID 1674302 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-aca8a20c14b0439d9b12b395730d21e9
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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