Dimethylformamide → 4-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-(s)-thiazolidine-3-carboxylic acid tert-butyl ester

HRID 1791370Notes

Reaction equation

CC(OC([CH:8]1[S:12][CH2:11][CH:10]([C:13]([OH:15])=O)[NH:9]1)=O)(C)C.[CH2:16](OC(Cl)=O)[CH:17]([CH3:19])[CH3:18].CN1CC[O:28]CC1.[C:31]([C:33]1[CH:34]=[C:35]([CH:40]=[CH:41][CH:42]=1)[C:36]([NH:38]O)=[NH:37])#[N:32].CN([CH:46]=[O:47])C>C1COCC1>[C:17]([O:28][C:46]([N:9]1[C@@H:10]([C:13]2[O:15][N:38]=[C:36]([C:35]3[CH:40]=[CH:41][CH:42]=[C:33]([C:31]#[N:32])[CH:34]=3)[N:37]=2)[CH2:11][S:12][CH2:8]1)=[O:47])([CH3:19])([CH3:18])[CH3:16]

Participants

Conditions

Temperature: 120 °C

Procedure

4-[3-(3-Cyano-phenyl)-[1,2,4]oxadiazol-5-yl]-(S)-thiazolidine-3-carboxylic acid tert-butyl ester (212 mg, 20%, yellow oil) was prepared according to the procedure in Example 25 from Boc-L-thiazolidine-4-carboxylic acid (696 mg, 2.98 mmol) with isobutylchloroformate (0.43 ml, 3.28 mmol) and N-methylmorpholine (0.36 ml, 3.28 mmol) in THF (5 ml) at 40° C. for 2 h. Then 3-cyano-N-hydroxy-benzamidine (577 mg, 3.58 mmol) and additional N-methylmorpholine (0.39 ml, 3.58 mmol) and THF (4 ml) at room temperature overnight followed by extraction of the product and addition of DMF (2 ml) and the mixture was heated at 120° C. overnight. The crude residue was purified on silica gel using 20% ethyl acetate.

Workup

customThe crude residue was purified on silica gel using 20% ethyl acetate

Sources & evidence

ORD record: ord-b04a569322c9446191de98fea4a5dc0b
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074809B2

Reaction notes

Loading…