Stannous Chloride → HCID 178507329, compound

HRID 1644605Notes

Reaction equation

Cl[Sn]Cl.[Cl:4][C:5]1[C:6]([C:11]2[CH:12]=[C:13]([C:20]3[NH:28][C:23]4=[N:24][CH:25]=[CH:26][CH:27]=[C:22]4[N:21]=3)[CH:14]=[C:15]([N+:17]([O-])=O)[CH:16]=2)=[N:7][CH:8]=[CH:9][CH:10]=1.C([O-])(O)=O.[Na+]>CCO>[Cl:4][C:5]1[C:6]([C:11]2[CH:16]=[C:15]([CH:14]=[C:13]([C:20]3[NH:28][C:23]4=[N:24][CH:25]=[CH:26][CH:27]=[C:22]4[N:21]=3)[CH:12]=2)[NH2:17])=[N:7][CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

SnCl2 (450 mg, 2.0 mmol) was added to a solution of Example 182 (140 mg, 0.4 mmol) in EtOH (5 mL) and the resulting suspension was heated at 100° C. for 3 h. The mixture was cooled to rt and saturated NaHCO3 solution (500 mL) was slowly added. The resulting milky white suspension was extracted with ethylacetate (3×100 mL). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The resulting material was purified by LCMS (acetonitrile-water gradient) to give the title compound (90 mg, 70%) as a white solid. 1H NMR (400 MHz, chloroform-d) δ ppm 7.31 (t, J=5.21 Hz, 1 H) 7.43 (dd, J=7.21, 4.42, Hz, 1 H) 7.55 (dd, J=5.27, 3.48 Hz, 1 H) 7.69 (t, J=5.11 Hz, 1 H) 7.86 (t, J=5.11 Hz, 1 H) 7.98 (dd, J=9.21, 5.42, Hz, 1 H) 8.56 (d, J=5.91 Hz, 1 H) 8.62 (d, J=5.91 Hz, 1 H). MS (ES) [M+H] calculated for C17H13ClN5, 322.01; found 321.98.

Workup

temperatureThe mixture was cooled to rt
extractionThe resulting milky white suspension was extracted with ethylacetate (3×100 mL)
washThe combined organic layers were washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting material was purified by LCMS (acetonitrile-water gradient)

Sources & evidence

ORD record: ord-02a53efe53624b9dae4413a1014265d5
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124617B2

Reaction notes

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