Phosphorus oxychloride → HCID 178515752, compound

HRID 1890332Notes

Reaction equation

C([O:8][C:9]1[N:14]=[C:13]2[N:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[C:16](=O)[NH:17][C:12]2=[CH:11][CH:10]=1)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:28]>>[Cl:28][C:16]1[N:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[C:13]2=[N:14][C:9]([OH:8])=[CH:10][CH:11]=[C:12]2[N:17]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 67312878HCID 67312878, compound

Product 1

HCID 178515752HCID 178515752, compoundYield 0.7%

Procedure

5-(Benzyloxy)-3-(2-chlorophenyl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (905 mg, 2.58 mmol) and POCl3 (1965 μl, 21.08 mmol) was heated in microwave at 100° C. for 1 h. The mixture was concentrated. The residue was dissolved in EtOAc and saturated NaHCO3. The organics were separated, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was dissolved in DCM (2.5 mL) and H2SO4 (6 drops) was added. The mixture was stirred vigorously for 15 minutes. DCM was removed by gentle heating. The residue was dissolved in MeOH and purified by preparative HPLC to give the title compound (5.0 mg). LCMS m/z=280.2, [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 6.63 (d, J=8.6 Hz, 1H), 7.63 (dd, J1=7.6, J2=1.6 Hz, 1H), 7.66 (td, J1=7.6, J2=1.8 Hz, 1H), 7.79 (m, 2H), 7.98 (d, J=8.6 Hz, 1H), 11.10 (broad s, 1H).

Workup

concentrationThe mixture was concentrated
dissolutionThe residue was dissolved in EtOAc
customThe organics were separated
washwashed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
dissolutionThe residue was dissolved in DCM (2.5 mL)
additionH2SO4 (6 drops) was added
customDCM was removed by gentle heating
dissolutionThe residue was dissolved in MeOH
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-4ef6de7f59fa414f91d7893ae918166d
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507473B2

Reaction notes

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