Diisopropylethylamine → HCID 178459262, compound

HRID 1412314Notes

Reaction equation

HRID 1412314 reaction equation
[CH3:1][C:2]1[N:40]=[C:5]2[N:6]([C@H:29]3[CH2:34][CH2:33][C@H:32]([O:35][CH2:36][C:37](=[O:39])[CH3:38])[CH2:31][CH2:30]3)[C:7](=[O:28])[C:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:16][CH:15]=3)=[C:9]([CH2:10][CH2:11][CH3:12])[N:4]2[N:3]=1.C(N(C(C)C)CC)(C)C.FC(F)(F)S(O[Si:56]([C:59]([CH3:62])([CH3:61])[CH3:60])([CH3:58])[CH3:57])(=O)=O>C(Cl)Cl.C(OCC)(=O)C>[Si:56]([O:39][C:37](=[CH2:38])[CH2:36][O:35][C@H:32]1[CH2:31][CH2:30][C@H:29]([N:6]2[C:7](=[O:28])[C:8]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:20]4[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:18][CH:19]=3)=[C:9]([CH2:10][CH2:11][CH3:12])[N:4]3[N:3]=[C:2]([CH3:1])[N:40]=[C:5]23)[CH2:34][CH2:33]1)([C:59]([CH3:62])([CH3:61])[CH3:60])([CH3:58])[CH3:57]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 178438632HCID 178438632, compound

Product 1

HCID 178459262HCID 178459262, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution (10 mL) of 4′-({2-methyl-5-oxo-4-[trans-4-(2-oxopropoxy)cyclohexyl]-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrile (0.56 g) and diisopropylethylamine (0.36 mL) in methylene chloride was added tert-butyl(dimethyl)silyl trifluoromethanesulfonate (0.36 mL), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.5 g, 72%).

Workup

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

Sources & evidence

ORD record
ord-d7cad3ba77a9488c8034714fd9681714
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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