HCID 44577825, compound → HCID 44577866, compound

HRID 877423Notes

Reaction equation

HRID 877423 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][C:8](=[O:25])[CH2:9][C:10]2[O:14][C:13]([C:15]3[N:20]=[C:19]([C:21]([O:23]C)=[O:22])[CH:18]=[CH:17][CH:16]=3)=[N:12][N:11]=2)=[CH:3][CH:2]=1>CO.C(Cl)Cl>[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][C:8](=[O:25])[CH2:9][C:10]2[O:14][C:13]([C:15]3[N:20]=[C:19]([C:21]([OH:23])=[O:22])[CH:18]=[CH:17][CH:16]=3)=[N:12][N:11]=2)=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 44577825HCID 44577825, compound

Product 1

HCID 44577866HCID 44577866, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared from 35 (4.5 mg, 0.010 mmol) following general procedure A. Flash chromatography (SiO2, 10% MeOH—CH2Cl2) afforded the title compound (3.4 mg, 85%) as a yellow solid: 1H NMR (DMSO-d6+0.1% TFA, 600 MHz) δ 8.29 (d, 1H, J=7.8 Hz), 8.17 (d, 1H, J=7.8 Hz), 8.08 (t, 1H, J=7.8 Hz), 7.57-7.55 (m, 4H), 7.36 (t, 2H, J=7.8 Hz), 7.29-7.25 (m, 2H), 4.02 (s, 4H); 13C NMR (DMSO-d6+0.1% TFA, 150 MHz) δ 202.1, 166.2, 164.7, 163.3, 150.0, 143.1, 142.2, 141.0, 139.9, 133.9, 131.1, 128.9, 128.0, 127.7, 127.5, 127.3, 126.7, 48.0, 39.8; HRMS-ESI-TOF m/z 400.1299 ([M+H]+, C23H17N3O4 requires 400.1292).

Sources & evidence

ORD record
ord-c278d759a4bd47ffb5423018606ad71f
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

Loading…