Hydrogen Sulfide → 2-(3-Methyl-[1,2,4]thiadiazol-5-yl)-7-thiocarbamoyl heptanoic acid phenylamide

HRID 1639576Notes

Reaction equation

[C:1]1([NH:7][C:8](=[O:23])[CH:9]([C:17]2[S:21][N:20]=[C:19]([CH3:22])[N:18]=2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]#[N:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[SH2:24]>N1C=CC=CC=1.N1CCCCC1>[C:1]1([NH:7][C:8](=[O:23])[CH:9]([C:17]2[S:21][N:20]=[C:19]([CH3:22])[N:18]=2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[S:24])[NH2:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred mixture of 7-cyano-2-(3-methyl[1,2,4]thiadiazol-5-yl)heptanoic acid phenylamide (2021044) (0.55 g, 1.7 mmol) in pyridine (120 mL) and piperidine (30 mL) was slowly bubbled hydrogen sulphide for 15 min. The resultant mixture was then stoppered and stirred at 50° C. for five days. The solvent was removed under reduced pressure, water (150 mL) was added to the residue, and the resultant solution was extracted with dichloromethane (3×150 mL). The crude product (1.6 g) was purified by preparative liquid chromatography to afford 2-(3-methyl-[1,2,4]thiadiazol-5-yl)-7-thiocarbamoyl heptanoic acid phenylamide (2021036) as a white solid.

Workup

customfor 15 min
customThe solvent was removed under reduced pressure, water (150 mL)
additionwas added to the residue
extractionthe resultant solution was extracted with dichloromethane (3×150 mL)
customThe crude product (1.6 g) was purified by preparative liquid chromatography

Sources & evidence

ORD record: ord-ddac096b9cb94c1fa2d88ed8f63b202b
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110577B2

Reaction notes

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