Water → HCID 178452235, compound

HRID 902652Notes

Reaction equation

HRID 902652 reaction equation
[N:1]1([C:7]2[N:12]=[C:11]([OH:13])[CH:10]=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[O:14](C(OC(C)(C)C)=O)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=O.O>O1CCOCC1>[C:18]([O:17][C:15]([N:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([OH:13])[N:12]=2)[CH2:6][CH2:5]1)=[O:14])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 90495Di-tert-butyl dicarbonateHCID 178516080HCID 178516080, compound

Product 1

HCID 178452235HCID 178452235, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

To a stirring solution of 6-piperazin-1-yl-pyridin-2-ol (0.6 g, 3.30 mmol—Pavia, M. R., Taylor, C. P., Hershenson, F. M., Lobbestael, S. J. J. Med. Chem. 1987, 30(7), 1210) in 1,4-dioxane (15 ml) was added t-BOC2O (0.80 g, 3.68 mmol) and H2O (3 ml). The reaction mixture was heated at 75° C. for 8 h and cooled to RT. The heterogenous mixture was filtered and concentrated. Purification by flash silica gel chromatography afforded the title compound as a red solid, 0.90 g (97%). MS (ESI) 280.4 (M+H+).

Workup

  1. temperaturecooled to RT
  2. filtrationThe heterogenous mixture was filtered
  3. concentrationconcentrated
  4. customPurification by flash silica gel chromatography

Sources & evidence

ORD record
ord-c3a6b4d465b245ae86627402b620c471
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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