Hydrochloric Acid → HCID 178432623, compound

HRID 2377978Notes

Reaction equation

HRID 2377978 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8]C)[C:3]=1[C:10]1[NH:11][C:12]([CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[C:13]([CH3:15])[N:14]=1.Cl.C(N(CC)CC)C.[NH2:31][CH2:32][C@H:33]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[CH:36]=1)[OH:34]>C(O)(=O)C>[Cl:41][C:37]1[CH:36]=[C:35]([C@H:33]([OH:34])[CH2:32][NH:31][C:2]2[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=2[C:10]2[NH:11][C:12]([CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[C:13]([CH3:15])[N:14]=2)[CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 9855591(S)-2-amino-1-(3-chlorophenyl)ethanolHCID 178494187HCID 178494187, compound

Product 1

HCID 178432623HCID 178432623, compoundYield 11.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

4-((2-(4-Iodo-2-methoxypyridin-3-yl)-4-methyl-1H-imidazol-5-yl)methyl)morpholine (0.008 g, 0.019 mmol) was dissolved in acetic acid (2 mL) and concentrated hydrochloric acid (2 mL) and this mixture was stirred at 90° C. for 2 hours. The mixture was then evaporated and the residue was dissolved in 1-methyl-2-pyrrolidone (4 mL) and treated with triethylamine (100 μL, 0.72 mmol) and the hydrochloric acid salt of (S)-2-amino-1-[3-chlorophenyl]ethanol (0.010 g, 0.048 mmol). The mixture was heated at 90° C. for 4 hours, then the solvent was evaporated and the residue was purified by Prep HPLC (ammonium acetate/acetonitrile/water) to give the title compound (0.001 g, 11%) as a white solid. HPLC<95% (220 nm), LCMS (+ESI, M+H+) m/z 444; 1H NMR (400 MHz, methanol-d4) δ (ppm): 2.21 (3H, br s), 2.56 (˜4H, br s), 3.46 (2H, br s), 3.49 (1H, dd, J=6.8 and 13.6 Hz), 3.55 (1H, dd, J=5.3 and 13.6 Hz), 3.61 (4H, br s), 4.79-4.84 (1H, m overlapped by D2O), 6.08 (1H, d, J=7.3 Hz), 7.06 (1H, d, J=7.6 Hz), 7.16 (1H, dt, J=8.4 and 1.8 Hz), 7.20 (1J, t, J=7.7 Hz), 7.27 (1H, br d, J=8.3 Hz), 7.39 (1H, br s).

Workup

  1. customThe mixture was then evaporated
  2. dissolutionthe residue was dissolved in 1-methyl-2-pyrrolidone (4 mL)
  3. customthe solvent was evaporated
  4. customthe residue was purified by Prep HPLC (ammonium acetate/acetonitrile/water)

Sources & evidence

ORD record
ord-2c4f5b3b3faf4d9b9818ad3d379ebf16
Source dataset
uspto-grants-2008_12
Patent number
US07470713B2

Reaction notes

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