HCID 44577826, compound → HCID 44577867, compound

HRID 877421Notes

Reaction equation

HRID 877421 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]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][CH:8]([OH: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 44577826HCID 44577826, compound

Product 1

HCID 44577867HCID 44577867, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared from 36 (7.5 mg, 0.017 mmol) following general procedure A. Flash chromatography (SiO2, 5% MeOH—CH2Cl2) afforded the title compound (6.5 mg, 95%) as a white solid: 1H NMR (DMSO-d6, 600 MHz) δ 8.26 (dd, 1H, J=8.4 Hz), 8.16 (dd, 1H, J=8.4 Hz), 8.06 (t, 1H, J=7.8 Hz), 7.55-7.51 (m, 4H), 7.36-7.33 (m, 3H), 7.24 (t, 1H, J=7.2 Hz), 4.26-4.22 (m, 1H), 3.13-2.99 (m, 2H), 2.86-2.84 (m, 2H); 13C NMR (DMSO-d6, 150 MHz) δ 167.2, 166.2, 164.2, 149.9, 144.1, 141.1, 139.6, 139.2, 138.7, 130.9, 129.5, 127.9, 127.5, 127.3, 126.3, 70.2, 43.4, 33.7; HRMS-ESI-TOF m/z 402.1443 ([M+H]+, C23H19N3O4 requires 402.1448).

Sources & evidence

ORD record
ord-d2a950536d5c49c8a1805ad6e4848dd5
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

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