1,4-Dioxane hydrochloride → HCID 44190324, compound

HRID 1816980Notes

Reaction equation

HRID 1816980 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C@@H:11]3[CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][C@@H:10]3[CH2:9]2)[CH:5]=[N:6][CH:7]=1.[ClH:23].O1CCOCC1>C(OCC)(=O)C.CO>[ClH:23].[ClH:23].[OH:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:9][C@@H:10]3[C@@H:11]([CH2:13][NH:14][CH2:15]3)[CH2:12]2)[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 44189742HCID 44189742, compound

Product 1

HCID 44190324HCID 44190324, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

The product from Example 6B (150 mg, 0.49 mmol) in ethyl acetate:methanol (1:2, 15 mL) was treated with HCl/1,4-dioxane (4M, 1 mL, 4 mmol). The mixture was stirred at ambient temperature overnight and then cooled in ice to complete precipitation. The mixture was filtered to provide the title compound as a white solid (136 mg, 99% yield). 1H NMR (CD3OD, 300 MHz) δ 3.30 (m, 4H), 3.51 (dd, J=10, 3 Hz, 2H), 3.60 (m, 4H), 7.06 (t, J=3 Hz, 1H), 7.62 (d, J=3 Hz, 1H), 7.69 (d, J=3 Hz, 1H); MS (DCI/NH3) m/z 206 (M+H)+; Anal. calculated for C11H15N3O.2 HCl.0.5H2O: C, 46.01; H, 6.32; N, 14.63. Found: C, 46.29; H, 6.49; N, 14.33.

Workup

  1. temperaturecooled in ice
  2. customprecipitation
  3. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-5886c9b3915748a4ae56aa66970e2a77
Source dataset
uspto-grants-2009_10
Patent number
US07598236B2

Reaction notes

Loading…