Triethylamine → HCID 58368678, compound

HRID 1192659Notes

Reaction equation

HRID 1192659 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=[O:14])[CH3:13])[C:9]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH:21]1([C:25](Cl)=[O:26])[CH2:24][CH2:23][CH2:22]1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=[O:14])[CH3:13])[C:9]([N:15]2[CH2:16][CH2:17][N:18]([C:25]([CH:21]3[CH2:24][CH2:23][CH2:22]3)=[O:26])[CH2:19][CH2:20]2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78705Cyclobutanecarbonyl chlorideHCID 67301190HCID 67301190, compound

Product 1

HCID 58368678HCID 58368678, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(5-chloro-8-piperazin-1-ylquinolin-7-yl)ethanone (0.063 g, 0.22 mmol, from Example 47, Step 1) was combined with cyclobutanecarboxylic acid chloride (0.037 mL, 0.32 mmol) and triethylamine (0.090 mL, 0.64 mmol) in methylene chloride (1.0 mL) at room temperature and stirred for 2 hours. The reaction was diluted with dichloromethane, washed with water, dried over MgSO4 and then concentrated. The resulted residue was purified on silica gel (eluting with 0 to 5% methanol in dichloromethane) to give the desired product (18 mg, 22%). LCMS calculated for C20H23ClN3O2 (M+H)+: m/z=372.1; Found: 372.1.

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe resulted residue was purified on silica gel (eluting with 0 to 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-4dd95b8a33954e04a83e561d8360173f
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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