Potassium Carbonate → HCID 68894696, compound

HRID 2220213Notes

Reaction equation

[C:1]([N:4]1[CH2:11][C:10]2[CH:12]=[C:13]([C:16]3[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=3[C:18](O)=[O:19])[CH:14]=[CH:15][C:9]=2[CH:8]=[CH:7][C:6]2[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:5]1=2)(=[O:3])[CH3:2].C(Cl)(=O)C(Cl)=O.C([O-])([O-])=O.[K+].[K+].[N:42]1[CH:47]=[CH:46]C=NN=1>C(Cl)Cl.CN(C=O)C.O>[C:1]([N:4]1[CH2:11][C:10]2[CH:12]=[C:13]([C:16]3[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=3[C:18]3[O:19][CH:46]=[CH:47][N:42]=3)[CH:14]=[CH:15][C:9]=2[CH:8]=[CH:7][C:6]2[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:5]1=2)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of Example 222 (20 mg, 0.05 mmol) in CH2Cl2 (1 mL) was added one drop of DMF. The solution was cooled to 0° C., oxalyl chloride (3 μl, 0.055 mmol) was added and the reaction mixture was stirred for 30 minutes. The reaction mixture was concentrated to a yellow solid, taken up in sulfolane and treated with K2CO3 (14 mg, 0.1 mmol) and 1,2,3-triazine (3 μl, 0.05 mmol). The mixture was heated at 140° C. for 5 hours, then water was added. The resulting mixture was filtered, and the solid was purified by preparative reversed-phase HPLC to give the title compound (3.3 mg, 15%). HPLC Rt=2.36 (b) min. m/z=427 (M+H+).

Workup

concentrationThe reaction mixture was concentrated to a yellow solid
temperatureThe mixture was heated at 140° C. for 5 hours
filtrationThe resulting mixture was filtered
customthe solid was purified by preparative reversed-phase HPLC

Sources & evidence

ORD record: ord-7f409d6e20a043bea2378176e0464fa0
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417040B2

Reaction notes

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