Hydrochloric Acid → HCID 178432624, compound

HRID 2377979Notes

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]([C:16]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[O:17])=[C:13]([CH3:15])[N:14]=1.Cl.C(N(CC)CC)C.[NH2:32][CH2:33][C@H:34]([C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=1)[OH:35]>C(O)(=O)C>[Cl:42][C:38]1[CH:37]=[C:36]([C@H:34]([OH:35])[CH2:33][NH:32][C:2]2[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=2[C:10]2[NH:11][C:12]([C:16]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:41]=[CH:40][CH:39]=1

Participants

Conditions

Temperature: 90 °C

Procedure

(2-(4-Iodo-2-methoxypyridin-3-yl)-4-methyl-1H-imidazol-5-yl)(morpholino)methanone (0.007 g, 0.017 mmol) was dissolved in acetic acid (1 mL) and concentrated hydrochloric acid (1 mL) and this mixture was stirred at 100° C. for 1 hour. The mixture was then evaporated and the residue was dissolved in N,N-dimethylformamide (2 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 (0.002 g, 25%) as a white solid. HPLC 100% (220 nm), LCMS (+ESI, M+H+) m/z 458; 1H NMR (400 MHz, methanol-d4) δ (ppm): 2.37 (3H, s), 3.45-4.0 (10H, m), 4.7-4.9 (1H, m, overlapped by D2O), 6.10 (1H, d, J=7.8 Hz), 7.10 (1H, d, J=7.6 Hz), 7.14-7.24 (3H, m), 7.36 (1H, s), 10.26 (1H, br s).

Workup

customThe mixture was then evaporated
dissolutionthe residue was dissolved in N,N-dimethylformamide (2 mL)
customthe solvent was evaporated
customthe residue was purified by Prep HPLC (ammonium acetate/acetonitrile/water)

Sources & evidence

ORD record: ord-2cdc9b6f03c6489ea133cd53c42cfb87
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470713B2

Reaction notes

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