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Hydrochloric Acid → 2-(4-(6-(4-(3-Isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)-5-nitropyrimidin-4-yloxy)phenyl)propane-1,3-diol

HRID 1619439
Notes
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Reaction equation

HRID 1619439 reaction equation
CC1(C)[O:7][CH2:6][CH:5]([C:8]2[CH:37]=[CH:36][C:11]([O:12][C:13]3[N:18]=[CH:17][N:16]=[C:15]([N:19]4[CH2:24][CH2:23][CH:22]([C:25]5[O:29][N:28]=[C:27]([CH:30]([CH3:32])[CH3:31])[N:26]=5)[CH2:21][CH2:20]4)[C:14]=3[N+:33]([O-:35])=[O:34])=[CH:10][CH:9]=2)[CH2:4][O:3]1.Cl>CC(C)=O>[CH:30]([C:27]1[N:26]=[C:25]([CH:22]2[CH2:21][CH2:20][N:19]([C:15]3[N:16]=[CH:17][N:18]=[C:13]([O:12][C:11]4[CH:36]=[CH:37][C:8]([CH:5]([CH2:6][OH:7])[CH2:4][OH:3])=[CH:9][CH:10]=4)[C:14]=3[N+:33]([O-:35])=[O:34])[CH2:24][CH2:23]2)[O:29][N:28]=1)([CH3:32])[CH3:31]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 675155835-(1-(6-(4-(2,2-Dimethyl-1,3-dioxan-5-yl)phenoxy)-5-nitropyrimidin-4-yl)piperidin-4-yl)-3-isopropyl-1,2,4-oxadiazole

Product 1

HCID 675166662-(4-(6-(4-(3-Isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)-5-nitropyrimidin-4-yloxy)phenyl)propane-1,3-diolYield 5.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
27 °C

Procedure

To a solution of 5-(1-(6-(4-(2,2-dimethyl-1,3-dioxan-5-yl)phenoxy)-5-nitropyrimidin-4-yl)piperidin-4-yl)-3-isopropyl-1,2,4-oxadiazole (500 mg, 0.0095 moles) in acetone (10 ml) was added conc. HCl (3 ml) and the reaction mixture was stirred for 4 hours at 27° C. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate. The organic extract was successively washed with water & brine, dried over sodium sulfate and evaporated under reduced pressure to yield 250 mg product as yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. extractionThe organic extract
  4. washwas successively washed with water & brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2b149ae611a24626a9b7690305d5aaa4
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08772302B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes