1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-[(4-{2-[(5-Bromopyridin-2-yl)amino]-2-oxoethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

HRID 914392Notes

Reaction equation

HRID 914392 reaction equation
[C:1]([O:5][C:6](=[O:20])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17]([OH:19])=O)[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][N:23]=1.CN(C)CCCN=C=NCC>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6](=[O:20])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][N:23]=2)=[O:19])[N:15]=1)([CH3:8])[CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 706222-Amino-5-bromopyridineHCID 59759443{2-[(2-Tert-butoxy-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}acetic acid

Product 1

HCID 597592352-[(4-{2-[(5-Bromopyridin-2-yl)amino]-2-oxoethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl esterYield 92.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

{2-[(2-tert-Butoxy-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}acetic acid (16 g) obtained in Example 3 and 2-amino-5-bromopyridine (8.7 g) were dissolved in dichloromethane (100 mL), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (EDC) hydrochloride (14.5 g) and 4-dimethylaminopyridine (DMAP) (9.2 g) was successively added, and the mixture was stirred at room temperature for 6 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=2:1) to give the title compound (22 g) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-f6c3cea6fae94e97861856b0b4e07fd8
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

Loading…