HCID 24949228, compound → HCID 24949377, compound

HRID 877403Notes

Reaction equation

HRID 877403 reaction equation
[C:1]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]([C:11]2[O:15][C:14]([C:16]3[N:21]=[C:20]([C:22]([O:24]C)=[O:23])[CH:19]=[CH:18][CH:17]=3)=[N:13][N:12]=2)=[O:10])=[CH:3][CH:2]=1>CC(O)=O.CCOC(C)=O>[C:1]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:2]=[CH:3][C:4]([CH2:7][CH2:8][C:9]([C:11]2[O:15][C:14]([C:16]3[N:21]=[C:20]([C:22]([OH:24])=[O:23])[CH:19]=[CH:18][CH:17]=3)=[N:13][N:12]=2)=[O:10])=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 24949228HCID 24949228, compound

Product 1

HCID 24949377HCID 24949377, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 22609514Ethyl acetate acetateSolvent

Procedure

The title compound was prepared from 28 (8.7 mg, 0.021 mmol) following general procedure A. Preparative thin layer chromatography (SiO2, 0-4% AcOH-EtOAc) afforded the title compound (8.4 mg, 100%) as a white solid: 1H NMR (DMSO-d6+0.1% TFA, 600 MHz) δ 8.32 (d, 1H, J=7.7 Hz), 8.17 (d, 1H, J=7.8 Hz), 8.01 (t, 1H, J=7.9 Hz), 7.85 (br s, 1H), 7.48 (d, 2H, J=7.4 Hz), 7.45 (d, 2H, J=8.1 Hz), 7.28 (t, 2H, J=7.7 Hz), 7.25 (d, 2H, J=8.1 Hz), 7.18 (t, 1H, J=7.3 Hz), 3.45 (t, 2H, J=7.4 Hz), 3.01 (t, 2H, J=7.4 Hz); 13C NMR (DMSO-d6+0.1% TFA, 150 MHz) δ 188.0, 167.0, 166.1, 165.0, 163.0, 151.1, 144.2, 142.1, 141.2, 140.5, 140.4, 130.6, 130.4, 129.2, 128.8, 128.5, 128.2, 44.7, 29.9; HRMS-ESI-TOF m/z 400.1288 ([M+H]+, C23H17N3O4 requires 400.1292).

Sources & evidence

ORD record
ord-0fce70b5b0db47a39ecc09e3e23841ed
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

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