Triethylamine → HCID 58368586, compound

HRID 1192684Notes

Reaction equation

HRID 1192684 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.[CH3:21][C:22]1[O:26][N:25]=[C:24]([C:27](Cl)=[O:28])[CH:23]=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:27]([C:24]3[CH:23]=[C:22]([CH3:21])[O:26][N:25]=3)=[O:28])[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 27368945-Methylisoxazole-3-carbonyl chlorideHCID 67301190HCID 67301190, compound

Product 1

HCID 58368586HCID 58368586, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(5-Chloro-8-piperazin-1-ylquinolin-7-yl)ethanone (0.030 g, 0.10 mmol from Example 47, Step 1) was combined with 5-methylisoxazole-3-carbonyl chloride (0.023 g, 0.16 mmol) and triethylamine (0.043 mL, 0.31 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, concentrated and purified on silica gel (0 to 5% methanol in dichloromethane) to give the desired product (32 mg, 77%). LCMS calculated for C20H20ClN4O3 (M+H)+: m/z=399.1; Found: 399.1.

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. custompurified on silica gel (0 to 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-65edccc4735344e182044c2519813f31
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

Loading…