Triethylamine → HCID 18790537, compound

HRID 1106981Notes

Reaction equation

HRID 1106981 reaction equation
Cl.[N:2]1([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:27])[CH2:15][S:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=[CH:19][CH:18]=3)=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[C:35](Cl)(=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37]>CC(C)=O>[C:35]([N:5]1[CH2:6][CH2:7][N:2]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:27])[CH2:15][S:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=[CH:19][CH:18]=3)=[CH:10][CH:9]=2)[CH2:3][CH2:4]1)(=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 18790534HCID 18790534, compound2×

Product 1

HCID 18790537HCID 18790537, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-[2-[4-(1-Piperazinyl)phenyl]-2-oxoethylthio]-quinoline hydrochloride (Compound 51; 2.20 g, 4.66 mmol) was suspended in dry acetone (300 ml). Triethylamine (6.60 ml, 47.2 mmol) was added at -15° C. to the suspension and, after 30 minutes, pivaloylchloride (1.25 ml, 10.0 mmol) was added dropwise to the suspension. The reaction mixture was stirred at room temperature overnight and the solvent was removed under reduced pressure. The residue was chromatographed by silica gel chromatography (dichloromethane:methanol=20:1) to obtain 1.50 g of the titled compound (72.0%).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was chromatographed by silica gel chromatography (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-ea79ec78918e428495258ad877fceb4f
Source dataset
uspto-grants-2000_05
Patent number
US06057447

Reaction notes

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