1-Iodoheptane → 2-[(4-{2-[(3-Chloro-5-methoxycarbonylpyridin-2-yl)(heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

HRID 914414Notes

Reaction equation

HRID 914414 reaction equation
[C:1]([O:5][C:6](=[O:19])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][NH2:18])[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].Cl[C:21]1[C:26]([Cl:27])=[CH:25][C:24]([C:28]([O:30][CH3:31])=[O:29])=[CH:23][N:22]=1.[CH2:32](I)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].CC(C)([O-])C.[K+]>CN(C)C=O.O>[C:1]([O:5][C:6](=[O:19])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][N:18]([C:21]2[C:26]([Cl:27])=[CH:25][C:24]([C:28]([O:30][CH3:31])=[O:29])=[CH:23][N:22]=2)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[N:15]=1)([CH3:9])[CH3:8])([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 202741-IodoheptaneHCID 2782166Methyl 5,6-DichloronicotinateHCID 23665647Potassium tert-butoxideHCID 597594492-{[4-(2-Aminoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

Product 1

HCID 597592482-[(4-{2-[(3-Chloro-5-methoxycarbonylpyridin-2-yl)(heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-[(4-{2-[(3-Chloro-5-methoxycarbonylpyridin-2-yl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (5.14 g) was obtained using 2-{[4-(2-aminoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (5 g) synthesized in Example 7 and 2,3-dichloro-5-(methoxycarbonyl)pyridine (3.41 g) as starting materials and by an operation similar to that of Example 265-1. The obtained compound (5.14 g) and heptyl iodide (1.86 mL) were dissolved in N,N-dimethylformamide (40 mL), potassium tert-butoxide (1.34 g) was added thereto, and the mixture was stirred at room temperature for 12 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=9:1) to give the title compound (2.59 g) as a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-bf9509e423d94dfe92acf582b27a99df
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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