4-Methylmorpholine → HCID 68487138, compound

O-(7-Azabenzotriazol1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (80 mg, 0.21 mmol) was added under stirring to a solution of 1H-benzoimidazol-1-ylacetic acid triethylammonium salt (55.5 mg, 0.2 mmol) and N-methyl morpholine (66 μL, 0.6 mmol) in acetonitrile (1 mL). After 5 min 1-heptylamine (30 μL, 0.2 mmol) was added and mixture was stirred at ambient temperature for 3 h. The solvent was evaporated, the residue was dissolved in ethyl acetate (15 mL) and extracted with saturated aqueous NaHCO3 (5 mL) and brine (5 mL) then dried over anhydrous Na2SO4 and concentrated. Purification of the crude product was performed by preparative HPLC (XTerra C8 column 19×300 mm, 0.1 M NH4OAc/CH3CN). Product-containing fractions were pooled and lyophilised affording the title compound (43.7 mg, 80%). Calculated for C16H23N3O m/z: 273.18, found 274.03 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.85 (m, 3H), 1.26 (m, 8 H), 1.41 (m, 2H), 3.07 (m, 2H), 4.88 (s, 2H), 7.20 (m, 2H), 7.42 (m, 1H), 7.64 (m, 1H), 8.14 (s, 1H), 8.27 (t, J=5.6 Hz, 1H).

1. customThe solvent was evaporated
2. dissolutionthe residue was dissolved in ethyl acetate (15 mL)
3. extractionextracted with saturated aqueous NaHCO3 (5 mL) and brine (5 mL)
4. dry with materialthen dried over anhydrous Na2SO4
5. concentrationconcentrated
6. customPurification of the crude product

ORD record

ord-2d6fac92103e4a589e90f8432a02080c

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07645784B2