Hydrochloric Acid → HCID 58486069, compound

HRID 655340Notes

Reaction equation

HRID 655340 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:12][C:13]3[CH:14]=[C:15]([C:19]4[N:24]=[CH:23][C:22]([N:25]5[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]5)=[CH:21][N:20]=4)[CH:16]=[CH:17][CH:18]=3)[C:9](=[O:11])[O:10][C:5]2=[CH:4][CH:3]=1.Cl>C(#N)C.O1CCOCC1>[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]4[N:24]=[CH:23][C:22]([N:25]5[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]5)=[CH:21][N:20]=4)[CH:14]=3)[C:9](=[O:11])[O:10][C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58486075HCID 58486075, compound

Product 1

HCID 58486069HCID 58486069, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

80 mg (0.16 mmol) of tert-butyl 4-{2-[3-(5-methyl-2-oxooxazolo[4,5-b]pyridin-3-ylmethyl)phenyl]pyrimidin-5-yl}piperazine-1-carboxylate are dissolved in 6 ml of acetonitrile, and 6 ml of 4 M HCl in dioxane are added. The reaction mixture is stirred at room temperature for 1 h and evaporated. The residue is taken up in water and ethyl acetate, and the water phase is adjusted to pH 12 using NaOH and extracted with ethyl acetate and dichloromethane. The organic phases are combined, dried over sodium sulfate and purified by column chromatography.

Workup

  1. customevaporated
  2. extractionextracted with ethyl acetate and dichloromethane
  3. dry with materialdried over sodium sulfate
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-d207d9367bd049f78275c70d9168d592
Source dataset
uspto-grants-2011_12
Patent number
US08071593B2

Reaction notes

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