Morpholine → HCID 178494188, compound

HRID 2377972Notes

Reaction equation

HRID 2377972 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

5

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 2724699PyBOPHCID 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).

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on Prep HPLC (ammonium acetate/acetonitrile/water)

Sources & evidence

ORD record
ord-da616716293a4759b72b59ba69eb88a3
Source dataset
uspto-grants-2008_12
Patent number
US07470713B2

Reaction notes

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