Triethylamine → 1-(5-Fluoro-8-{4-[(1-methyl-1H-pyrazol-4-yl)carbonyl]piperazin-1-yl}quinolin-7-yl)ethanone

HRID 1192694Notes

Reaction equation

HRID 1192694 reaction equation
[F: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][N:22]1[CH:26]=[C:25]([C:27](Cl)=[O:28])[CH:24]=[N:23]1.C(N(CC)CC)C>ClCCl>[F: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:25]3[CH:24]=[N:23][N:22]([CH3:21])[CH:26]=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 31649311-methyl-1H-pyrazole-4-carbonyl chlorideHCID 583686261-(5-Fluoro-8-piperazin-1-ylquinolin-7-yl)ethanone

Product 1

HCID 583685681-(5-Fluoro-8-{4-[(1-methyl-1H-pyrazol-4-yl)carbonyl]piperazin-1-yl}quinolin-7-yl)ethanoneYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(5-Fluoro-8-piperazin-1-ylquinolin-7-yl)ethanone (0.038 g, 0.14 mmol) was combined with 1-methyl-1H-pyrazole-4-carbonyl chloride (0.030 g, 0.21 mmol) and triethylamine (0.058 mL, 0.42 mmol) in methylene chloride (1.0 mL, 16 mmol) at room temperature and stirred for 2 hrs. The reaction was diluted with dichloromethane, washed with water, dried over MgSO4, concentrated and purified on silica gel (eluting with 0 to 5% methanol in dichloromethane) to give the desired product (45 mg, 85%). LCMS calculated for C20H21FN5O2 (M+H)+: m/z=382.2; Found: 382.1.

Workup

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

Sources & evidence

ORD record
ord-d96f041335814b21904f398599e5c16a
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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