Hydrochloric Acid → 4-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-3-(1-hydroxy-5-phenyl-1H-imidazol-2-yl)-1H-pyridin-2-one

HRID 2377964Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8]C)[C:3]=1[C:10]1[N:11]([OH:21])[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:13][N:14]=1.C(N(CC)CC)C.Cl.[NH2:30][CH2:31][C@H:32]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=1)[OH:33]>CN(C)C=O>[Cl:40][C:36]1[CH:35]=[C:34]([CH:32]([OH:33])[CH2:31][NH:30][C:2]2[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=2[C:10]2[N:11]([OH:21])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][N:14]=2)[CH:39]=[CH:38][CH:37]=1

Participants

Conditions

Temperature: 65 °C

Procedure

2-(4-Iodo-2-methoxy-pyridin-3-yl)-5-phenyl-imidazol-1-ol (0.020 g, 0.053 mmol) was dissolved in N,N-dimethylformamide (4 mL) and treated with triethylamine (20 μL, 0.159 mmol) and the hydrochloric acid salt of (S)-2-amino-1-[3-chlorophenyl]ethanol (0.017 g, 0.0795 mmol). This mixture was heated at 65° C. for 3 hours, then the solvent was evaporated. The residue was purified by Prep HPLC (ammonium acetate/water/acetonitrile) to give the title material (0.006 g, 27%) as a beige solid. HPLC 87.9% (220 nm), LCMS (+ESI, M+H+) m/z 423; IR ν (cm−1): 2923, 2853, 1637; HRMS calcd for C22H20N4O3Cl (M+H)+=423.1224, found: 423.1221; 1H NMR (400 MHz, methanol-d4) δ (ppm): 3.56 (1H, dd, J=13.2 and 7.0 Hz), 3.69 (1H, dd, J=13.2 and 4.6 Hz), 4.96 (1H, m), 6.36 (1H, d, J=7.4 Hz), 7.22-7.79 (11H, m).

Workup

customthe solvent was evaporated
customThe residue was purified by Prep HPLC (ammonium acetate/water/acetonitrile)

Sources & evidence

ORD record: ord-db0f6c8555e34e178049acee9b8f8b4d
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470713B2

Reaction notes

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