1,2-Dichloroethane → 2,2-Dimethyl-N-[1-[6-(5-{2-[4-(trifluoromethyl)phenyl]ethyl}-1,2,4-oxadiazol-3-yl)quinolin-2-yl]pyrrolidin-3-yl}propanamide

HRID 6815

Reaction equation

[OH:1][NH:2][C:3](=[NH:26])[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([N:14]1[CH2:18][CH2:17][CH:16]([NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:15]1)[CH:8]=[CH:7]2.[F:27][C:28]([F:41])([F:40])[C:29]1[CH:34]=[CH:33][C:32]([CH:35]([CH3:39])C(O)=O)=[CH:31][CH:30]=1.[CH2:42](Cl)CCl>COCCOCCOC>[CH3:24][C:21]([CH3:22])([CH3:23])[C:20]([NH:19][CH:16]1[CH2:17][CH2:18][N:14]([C:9]2[CH:8]=[CH:7][C:6]3[C:11](=[CH:12][CH:13]=[C:4]([C:3]4[N:26]=[C:42]([CH2:39][CH2:35][C:32]5[CH:31]=[CH:30][C:29]([C:28]([F:27])([F:40])[F:41])=[CH:34][CH:33]=5)[O:1][N:2]=4)[CH:5]=3)[N:10]=2)[CH2:15]1)=[O:25]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of the product of Step E, (66 mg) in anhydrous diglyme (2 mL) was added 4-trifluoromethylphenylpropionic acid (1.1 eq.) and EDC (2 eq.). The reaction mixture was heated to 50° C. overnight. After approximately 18 h, the mixture was heated at 110° C. for 2 hr. The mixture was cooled to r.t., quenched with water and extracted with excess EtOAc. The combined extracts were dried over a drying agent filtered and the solvent removed under vacuum. The residue was purified by preparative TLC eluting with EtOAc to afford the product, MS: m/z 538.

Workup

temperaturethe mixture was heated at 110° C. for 2 hr
temperatureThe mixture was cooled to r.t.
customquenched with water
extractionextracted with excess EtOAc
customThe combined extracts were dried over a drying agent
filtrationfiltered
customthe solvent removed under vacuum
customThe residue was purified by preparative TLC
washeluting with EtOAc
customto afford the product, MS

Sources & evidence

ORD record: ord-5b2ee72421e84c96a53e63a90b2cd355
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084156B2

Linked notes

Loading…