HCID 24950525, compound → HCID 24951318, compound

HRID 877410Notes

Reaction equation

HRID 877410 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]2[S:19][C:18]([C:20]3[N:25]=[C:24]([C:26]([O:28]C)=[O:27])[CH:23]=[CH:22][CH:21]=3)=[N: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[S:19][C:18]([C:20]3[N:25]=[C:24]([C:26]([OH:28])=[O:27])[CH:23]=[CH:22][CH:21]=3)=[N:17][N:16]=2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 24950525HCID 24950525, compound

Product 1

HCID 24951318HCID 24951318, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 22609514Ethyl acetate acetateSolvent

Procedure

The title compound was prepared from 12f (8.7 mg, 0.021 mmol) following general procedure A. Preparative thin layer chromatography (SiO2, 0-2% AcOH-EtOAc) afforded the title compound (8.4 mg, 100%) as a white solid: 1H NMR (acetone-d6+0.1% TFA, 500 MHz) δ 8.64 (dd, 1H, J=1.8, 7.2 Hz), 8.34 (m, 2H), 7.25 (m, 2H), 7.20 (dd, 2H, J=3.0, 5.1 Hz), 7.14 (t, 1H, J=7.2 Hz), 3.28 (t, 2H, J=7.3 Hz), 2.62 (t, 2H, J=7.7 Hz), 1.80 (m, 2H), 1.65 (m, 2H), 1.45 (m, 4H); 13C NMR (acetone-d6+0.1% TFA, 150 MHz) δ 195.2, 174.9, 171.9, 166.1, 150.4, 150.1, 144.5, 141.6, 130.2, 130.1, 128.9, 127.4, 126.4, 40.7, 37.4, 33.2, 31.3, 30.6, 25.4; HRMS-ESI-TOF m/z 396.1380 ([M+H]+, C21H21N3O3S requires 396.1376).

Sources & evidence

ORD record
ord-b67b7aafb70049409bc76322f8801268
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

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