HCID 178499162, compound → HCID 178520585, compound

HRID 877415Notes

Reaction equation

HRID 877415 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]2[NH:16][C:17](C(OC)=O)=[N:18][N:19]=2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CCOC(C)=O>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]2[NH:16][CH:17]=[N:18][N:19]=2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 178499162HCID 178499162, compound

Product 1

HCID 178520585HCID 178520585, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared by methyl ester hydrolysis and spontaneous decarboxylation from ketone 14h (9.0 mg, 0.03 mmol) following general procedure A. Preparative thin layer chromatography (SiO2, 100% EtOAc) afforded the title compound (4.5 mg, 52%) as a colorless oil: 1H NMR (CDCl3, 600 MHz) δ 8.47 (br s, 1H), 7.27 (m, 2H), 7.17 (m, 3H), 3.15 (t, 2H, J=7.4 Hz), 2.61 (t, 2H, J=7.7 Hz), 1.78 (m, 2H), 1.64 (m, 2H), 1.42 (m, 4H); 13C NMR (CDCl3, 150 MHz) δ 194.3, 157.2, 147.5, 142.8, 128.5, 128.4, 125.8, 39.7, 36.0, 31.4, 29.9, 29.2, 23.7; HRMS-ESI-TOF m/z 258.1599 ([M−H]−, C15H19N3O requires 258.1606).

Sources & evidence

ORD record
ord-575aa775db164db1a2498177faad5309
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

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