HCID 16110712, compound → HCID 16110657, compound

HRID 605649Notes

Reaction equation

HRID 605649 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]2[O:16][C:17]([C:20]3[N:29]=[CH:28][CH:27]=[CH:26][C:21]=3[C:22]([O:24]C)=[O:23])=[CH:18][N:19]=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[O:16][C:17]([C:20]3[N:29]=[CH:28][CH:27]=[CH:26][C:21]=3[C:22]([OH:24])=[O:23])=[CH:18][N:19]=2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 16110712HCID 16110712, compound

Product 1

HCID 16110657HCID 16110657, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 22609514Ethyl acetate acetateSolvent

Procedure

The title compound was prepared from methyl 2-(2-(7-phenylheptanoyl)oxazol-5-yl)nicotinate (8 mg, 0.020 mmol) following General Procedure E. Preparative thin layer chromatography (2% AcOH/EtOAc) yielded the title compound as a white solid (3 mg, 38%): 1H NMR (THF-d8, 600 MHz) δ 8.71 (d, 1H, J=4.8 Hz), 8.09 (d, 1H, J=7.8 Hz), 7.79 (s, 1H), 7.45-7.44 (m, 2H), 7.22-7.19 (m, 2H), 7.16-7.14 (m, 2H), 7.11-7.08 (m, 1H), 3.05 (t, 2H, J=7.8 Hz), 2.60 (t, 2H, J=7.2 Hz), 1.73-1.69 (m, 2H), 1.66-1.61 (m, 2H), 1.43-1.39 (m, 4H); 13C NMR (THF-d8, 150 MHz) δ 185.5, 165.6, 156.4, 150.9, 149.5, 142.7, 141.1, 135.7, 127.0, 126.7, 126.5, 125.9, 123.9, 121.9, 37.1, 24.3, 30.0, 27.6, 27.5, 22.2; MALDI-FTMS m/z 379.1646 (M+H+, C22H23N2O4, requires 379.1652).

Sources & evidence

ORD record
ord-98f10264663e4be1b89b895f92895e3b
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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