HCID 24951159, compound → HCID 24950363, compound

HRID 877404Notes

Reaction equation

HRID 877404 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]2[N:19]=[C:18]([C:20]3[N:25]=[C:24]([C:26]([O:28]C)=[O:27])[CH:23]=[CH:22][CH:21]=3)[O:17][N:16]=2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CC(O)=O.CCOC(C)=O>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]2[N:19]=[C:18]([C:20]3[N:25]=[C:24]([C:26]([OH:28])=[O:27])[CH:23]=[CH:22][CH:21]=3)[O:17][N:16]=2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 24951159HCID 24951159, compound

Product 1

HCID 24950363HCID 24950363, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 22609514Ethyl acetate acetateSolvent

Procedure

The title compound was prepared from 10f (5.2 mg, 0.008 mmol) following general procedure A. Flash chromatography (SiO2, 0.5×6 cm, 0-2% AcOH-EtOAc) afforded the title compound (3 mg, 99%) as a white solid: NMR (acetone-d6+0.1% TFA, 500 MHz) δ 8.58 (dd, 1H, J=1.0, 7.7 Hz), 8.44 (dd, 1H, J=1.1, 7.8 Hz), 8.38 (t, 1H, J=7.7 Hz), 7.25 (t, 2H, J=7.5 Hz), 7.20 (d, 2H, J=6.9 Hz), 7.14 (t, 1H, J=7.2 Hz), 3.18 (t, 2H, J=7.3 Hz), 2.63 (t, 2H, J=7.7 Hz), 1.78 (m, 2H), 1.65 (m, 2H), 1.44 (m, 4H); 13C NMR (acetone-d6+0.1% TFA, 150 MHz) δ 192.7, 176.7, 168.3, 166.2, 150.7, 144.7, 144.6, 141.8, 130.2, 130.1, 129.7, 129.6, 127.4, 42.4, 37.5, 33.2, 31.3, 30.5, 24.9; HRMS-ESI-TOF m/z 380.1601 ([M+H]+, C21H21N3O4 requires 380.1605).

Sources & evidence

ORD record
ord-cb46fde2bf244e5a9ccacb3cd0883021
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

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