Triethylamine → HCID 67398468, compound

HRID 914417Notes

Reaction equation

HRID 914417 reaction equation
[C:1]([O:5][C:6](=[O:36])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][N:18]([C:26]2[C:31]([Cl:32])=[CH:30][C:29]([C:33](=O)[NH2:34])=[CH:28][N:27]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[C:1]([O:5][C:6](=[O:36])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][N:18]([C:26]2[C:31]([Cl:32])=[CH:30][C:29]([C:33]#[N:34])=[CH:28][N:27]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:15]=1)([CH3:8])[CH3:9])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 59759337HCID 59759337, compound

Product 1

HCID 67398468HCID 67398468, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[(4-{2-[(5-Carbamoyl-3-chloropyridin-2-yl)(heptyl)amino)ethyl)-1,3-thiazol-2-yl)thio)-2-methylpropionic acid tert-butyl ester (0.85 g) synthesized in Example 281-2 was dissolved in dichloromethane (10 mL), triethylamine (0.26 mL), trifluoroacetic acid anhydride (0.24 mL) was added, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was washed with water, 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 (0.37 g).

Workup

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

Sources & evidence

ORD record
ord-a90d0a519d2d46bd96dbe8893f975256
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

Loading…