Hydrochloric Acid → HCID 21088584, compound

HRID 350752Notes

Reaction equation

HRID 350752 reaction equation
[S:1]1[CH2:5][CH2:4][NH:3][CH2:2]1.[N:6]1([C:15]2[O:16][C:17]([CH2:27][CH2:28][C:29](O)=[O:30])=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[N:19]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[CH:7]1.ON1C2N=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.Cl>CN(C)C=O>[N:6]1([C:15]2[O:16][C:17]([CH2:27][CH2:28][C:29]([N:3]3[CH2:4][CH2:5][S:1][CH2:2]3)=[O:30])=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[N:19]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[CH:7]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10444ThiazolidineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 21088585HCID 21088585, compound

Product 1

HCID 21088584HCID 21088584, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of thiazolidine (145 mg), 3-{3-[2-(1H-benzoimidazol-1-yl)-4-(4-chlorophenyl}-5-oxazolyl]propionic acid (300 mg), 1-hydroxy-7-aza-1H-1,2,3-benzotriazole (222 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (253 mg) and N,N-dimethylformamide (1 ml) was stirred overnight at room temperature. To the reaction mixture was added 0.1N aqueous hydrochloric acid solution (16 ml) and the reaction mixture was extracted with ethyl acetate (5 ml). The organic layer was concentrated, introduced into preparative HPLC and purified to give 3-{3-[2-(1H-benzoimidazol-1-yl)-4-(4-chlorophenyl)-5-oxazolyl]propanoyl}thiazolidine (165 mg, 46%). Recrystallization from ethyl acetate-hexane gave yellow prism crystals. melting point: 125–126° C.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (5 ml)
  2. concentrationThe organic layer was concentrated
  3. additionintroduced into preparative HPLC
  4. custompurified

Sources & evidence

ORD record
ord-b97852ece6334054b409144ca3f3fadb
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

Loading…