Triethylamine → HCID 15515892, compound

HRID 1815751Notes

Reaction equation

HRID 1815751 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[N:11]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[NH:14][CH2:13][CH2:12]2.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.O>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[N:14]1[CH:15]2[CH2:18][CH2:19][N:11]([CH2:17][CH2:16]2)[CH2:12][CH2:13]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 119872-ChlorobenzothiazoleHCID 3984071,4-Diazabicyclo(3.2.2)nonane

Product 1

HCID 15515892HCID 15515892, compoundYield 34.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

2-Chlorobenzothiazole (Aldrich, 109 μL, 0.841 mmol) was added to a solution of 1,4-diazabicyclo[3.2.2]nonane (57%, 169 mg, 0.765 mmol), Et3N (213 μL, 1.53 mmol) in DMF (2.5 mL). The reaction mixture was heated at 100° C. for 2 h. The mixture was allowed to cool to RT, diluted with EtOAc and H2O and the layers were partitioned. The aqueous layer was extracted with EtOAc (3×) and the combined organic extracts were washed successively with H2O and brine and then dried (Na2SO4), filtered and concentrated. The crude residue was purified by chromatography (Biotage, 12L) eluting with 5% MeOH in CHCl3 to afford 68 mg (34%) of the title compound as a yellow oil: 1H NMR (CDCl3, 400 MHz) δ 7.58 (d, 1H, J=7.9 Hz), 7.57 (d, 1H, J=7.9 Hz), 7.27 (t, 1H, J=8.3 Hz), 7.04 (td, 1H, J=7.9, 1.2 Hz), 4.31 (s, 1H), 3.92 (t, 2H, J=5.8 Hz), 3.19-2.98 (m, 6H), 2.25-2.16 (m, 2H), 1.84-1.77 (m, 2H), MS (Cl) m/z 260.2 (M+1). The hydrochloride salt was prepared by dissolving the title compound in iPrOH and adding 0.1 mL of 6 M hydrochloric acid.

Workup

  1. temperatureto cool to RT
  2. customthe layers were partitioned
  3. extractionThe aqueous layer was extracted with EtOAc (3×)
  4. washthe combined organic extracts were washed successively with H2O and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by chromatography (Biotage, 12L)
  9. washeluting with 5% MeOH in CHCl3

Sources & evidence

ORD record
ord-27b650790bc6466881a5764768ffb72c
Source dataset
uspto-grants-2005_04
Patent number
US06881734B2

Reaction notes

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