HCID 24951162, compound → HCID 24950523, compound

HRID 877406Notes

Reaction equation

HRID 877406 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]2[S:16][C:17]([C:20]3[N:25]=[C:24]([C:26]([O:28]C)=[O:27])[CH:23]=[CH:22][CH: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[S:16][C:17]([C:20]3[N:25]=[C:24]([C:26]([OH:28])=[O:27])[CH:23]=[CH:22][CH: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 24951162HCID 24951162, compound

Product 1

HCID 24950523HCID 24950523, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 22609514Ethyl acetate acetateSolvent

Procedure

The title compound was prepared from 11f (6.8 mg, 0.016 mmol) following general procedure A. Flash chromatography (SiO2, 0.5×6 cm, 0-2% AcOH-EtOAc) afforded the title compound (5.4 mg, 86%) as a white solid: 1H NMR (CDCl3, 400 MHz) δ 10.51 (s, 1H(—OH)), 8.46 (s, 1H), 8.23 (dd, 1H, J=0.9, 7.6 Hz), 8.07 (t, 1H, J=7.8 Hz), 8.00 (dd, 1H, J=0.9, 7.9 Hz), 7.27 (m, 2H), 7.17 (m, 3H), 3.16 (t, 2H, J=7.4 Hz), 2.61 (t, 2H, J=7.7 Hz), 1.79 (m, 2H), 1.65 (m, 2H), 1.42 (m, 4H); 13C NMR (CDCl3, 150 MHz) δ 194.3, 175.8, 168.6, 149.0, 146.7, 144.1, 142.8, 142.6, 139.9, 128.5, 128.4, 125.8, 124.7, 123.8, 38.4, 36.0, 31.4, 29.23, 29.17, 24.1; HRMS-ESI-TOF m/z 395.1436 ([M+H]+, C22H22N2O3S requires 395.1424). 1,3,4-Thiadiazoles (5a-5c, 12a-12, 25):

Sources & evidence

ORD record
ord-db6ea4ce68e74669a33979c20c6dc5ed
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

Loading…