HCID 44577826, compound → HCID 44577825, compound

HRID 877422Notes

Reaction equation

HRID 877422 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][CH:8]([OH:25])[CH2:9][C:10]2[O:14][C:13]([C:15]3[N:20]=[C:19]([C:21]([O:23][CH3:24])=[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]([O:23][CH3:24])=[O:22])[CH:18]=[CH:17][CH:16]=3)=[N:12][N:11]=2)=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 44577826HCID 44577826, compound

Product 1

HCID 44577825HCID 44577825, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared from 36 (22 mg, 0.052 mmol) following general procedure B. Flash chromatography (SiO2, 5% MeOH—CH2Cl2) afforded the title compound (10.2 mg, 47%) as a white solid: 1H NMR (CDCl3, 600 MHz) δ 8.39 (d, 1H, J=7.8 Hz), 8.25 (d, 1H, J=7.8 Hz), 8.02 (t, 1H, J=7.8 Hz), 7.59-7.54 (m, 4H), 7.44 (t, 2H, J=7.8 Hz), 7.36-7.30 (m, 2H), 4.19 (s, 2H), 4.02 (s, 3H), 3.93 (s, 2H); 13C NMR (CDCl3, 150 MHz) δ 199.1, 164.7, 164.1, 162.1, 148.5, 143.5, 140.5, 140.4, 138.4, 131.4, 129.9, 128.7, 127.7, 127.4 (2C), 127.1, 127.0 (2C), 126.1, 53.2, 49.4, 38.9; HRMS-ESI-TOF m/z 414.1460 ([M+H]+, C24H19N3O4 requires 414.1448).

Sources & evidence

ORD record
ord-c63aca9f5a6943a694d859ca155dafd6
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

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