HCID 16110713, compound → HCID 16110658, compound

HRID 605647Notes

Reaction equation

HRID 605647 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[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][N:21]=3)=[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[CH:29]=[CH:28][C:23]([C:24]([OH:26])=[O:25])=[CH:22][N:21]=3)=[CH:18][N:19]=2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 16110713HCID 16110713, compound

Product 1

HCID 16110658HCID 16110658, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 22609514Ethyl acetate acetateSolvent

Procedure

The title compound was prepared from methyl 6-(2-(7-phenylheptanoyl)oxazol-5-yl)nicotinate (10 mg, 0.025 mmol) following General Procedure E. Preparative thin layer chromatography (2% AcOH/EtOAc) yielded the title compound as a white solid (4 mg, 40%): 1H NMR (THF-d8, 500 MHz) δ 9.18 (s, 1H), 8.41 (d, 1H, J=8.0 Hz), 7.97-7.94 (m, 2H), 7.22-7.09 (m, 5H), 3.08 (t, 2H, J=7.5 Hz), 2.61 (t, 2H, J=7.5 Hz), 1.74-1.69 (m, 2H), 1.67-1.61 (m, 2H), 1.47-1.40 (m, 4H); 13C NMR (THF-d8, 125 MHz) δ 185.6, 163.6, 156.7, 151.1, 149.8, 147.9, 141.0, 136.7, 126.7, 126.5, 125.0, 123.9, 117.7, 37.2, 34.3, 29.9, 27.6, 27.5, 22.2; MALDI-FTMS m/z 379.1645 (M+H+, C22H23N2O4, requires 379.1652).

Sources & evidence

ORD record
ord-6dfef3282e4d459ab98e55df0305398c
Source dataset
uspto-grants-2011_03
Patent number
US07915270B2

Reaction notes

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