Triethylamine → HCID 59758990, compound

HRID 914391Notes

Reaction equation

HRID 914391 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[N:12]=[C:13]([S:16][C:17]([CH3:22])([CH3:21])[C:18]([OH:20])=[O:19])[S:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(N(CC)CC)C.Cl[C:31]1[C:36]([N+:37]([O-:39])=[O:38])=[CH:35][CH:34]=[CH:33][N:32]=1>C(#N)C>[CH2:1]([N:8]([C:31]1[C:36]([N+:37]([O-:39])=[O:38])=[CH:35][CH:34]=[CH:33][N:32]=1)[CH2:9][CH2:10][C:11]1[N:12]=[C:13]([S:16][C:17]([CH3:21])([CH3:22])[C:18]([OH:20])=[O:19])[S:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 796132-Chloro-3-nitropyridineHCID 67399150HCID 67399150, compound

Product 1

HCID 59758990HCID 59758990, compoundYield 0.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 2-({4-[2-(heptylamino)ethyl]-1,3-thiazol-2-yl}thio)-2-methylpropionic acid resin (0.15 g) synthesized in Example 461-6 in acetonitrile (1.5 ml) were added triethylamine (0.16 ml) and 2-chloro-3-nitropyridine (0.089 g), and the mixture was stirred at room temperature overnight. The resin was collected by filtration from the mixture, washed three times with dimethylformamide, tetrahydrofuran and methanol, and vacuum dried. Trifluoroacetic acid (2.0 mL) was added to the obtained resin, and the mixture was left standing at room temperature for 2 hr. Then the resin was removed by filtration from the reaction mixture, and the filtrate was concentrated by blowing a nitrogen gas, vacuum dried, and purified by preparative HPLC to give the title compound (1.5 mg) as a pale-brown oil.

Workup

  1. filtrationThe resin was collected by filtration from the mixture
  2. washwashed three times with dimethylformamide, tetrahydrofuran and methanol, and vacuum
  3. customdried
  4. additionTrifluoroacetic acid (2.0 mL) was added to the obtained resin
  5. waitthe mixture was left
  6. waitstanding at room temperature for 2 hr
  7. customThen the resin was removed by filtration from the reaction mixture
  8. concentrationthe filtrate was concentrated
  9. customdried
  10. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-243af8cffdef40d487b35152ecd17dc3
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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