HCID 24950528, compound → HCID 24948911, compound

HRID 877413Notes

Reaction equation

HRID 877413 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]2[N:20]=[N:19][C:18]([C:21]3[N:26]=[C:25]([C:27]([O:29]C)=[O:28])[CH:24]=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CCOCC>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]2[N:20]=[N:19][C:18]([C:21]3[N:26]=[C:25]([C:27]([OH:29])=[O:28])[CH:24]=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 24950528HCID 24950528, compound

Product 1

HCID 24948911HCID 24948911, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The title compound was prepared from 13f (1.9 mg, 0.0047 mmol) following general procedure A. Tritration with Et2O afforded the title compound (1.3 mg, 71%) as a white solid: 1H NMR (CDCl3, 600 MHz) δ 9.06 (d, 1H, J=7.8 Hz), 8.65 (d, 1H, J=8.7 Hz), 8.42 (d, 1H, J=7.5 Hz), 8.32 (d, 1H, J=8.7 Hz), 8.23 (t, 1H, J=7.8 Hz), 7.27 (m, 2H), 7.17 (m, 3H), 3.45 (t, 2H, J=7.4 Hz), 2.62 (t, 2H, J=7.8 Hz), 1.83 (m, 2H), 1.66 (m, 2H), 1.46 (m, 4H); 13C NMR (CDCl3, 150 MHz) δ 200.2, 163.5, 158.2, 155.7, 152.2, 146.4, 142.9, 140.2, 128.5, 128.4, 126.7, 126.0, 125.8, 125.7, 125.2, 38.5, 36.1, 31.5, 29.3, 29.2, 24.0; HRMS-ESI-TOF m/z 390.1811 ([M+H]+, C23H23N3O3 requires 390.1812).

Sources & evidence

ORD record
ord-500b698f94b14ddf933f726622bc9774
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

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