Morpholine → HCID 178494188, compound

Reaction equation

[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[NH:11][C:12]([C:16]([OH:18])=O)=[C:13]([CH3:15])[N:14]=1.C(N(CC)CC)C.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>>[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[NH:11][C:12]([C:16]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[O:18])=[C:13]([CH3:15])[N:14]=1

Participants

Reactant 4

HCID 8083Morpholine

HCID 8471Triethylamine

HCID 2724699PyBOP

HCID 178494191HCID 178494191, compound

Product 1

HCID 178494188HCID 178494188, compoundYield 52%

Procedure

To a stirred solution of 2-(4-iodo-2-methoxypyridin-3-yl)-4-methyl-1H-imidazole-5-carboxylic acid (0.039 g, 0.1085 mmol) in N,N-diemthylformamide (2 mL) was added triethylamine (60 mL, 0.434 mmol), morpholine (14 mL, 0.1627 mmol) and PyBOP (85 mgs, 0.1627 mmol) at room temperature. The reaction was stirred at room temperature for 10 minutes then the solvent was evaporated. The residue was dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified on Prep HPLC (ammonium acetate/acetonitrile/water) to give the title material (0.024 g, 52%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 2.32 (s, 3H) 3.54 (s, 8H) 3.76 (s, 3H) 7.55 (d, J=5.31 Hz, 1H) 7.87 (d, J=5.31 Hz, 1H).