Triethylamine → HCID 58368596, compound

HRID 1192674Notes

Reaction equation

HRID 1192674 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.[C:21]([N:24]1[CH2:29][CH2:28][CH:27]([C:30](Cl)=[O:31])[CH2:26][CH2:25]1)(=[O:23])[CH3:22].C(N(CC)CC)C>C(Cl)Cl>[C:21]([N:24]1[CH2:25][CH2:26][CH:27]([C:30]([N:18]2[CH2:17][CH2:16][N:15]([C:9]3[C:10]([C:12](=[O:14])[CH3:13])=[CH:11][C:2]([Cl:1])=[C:3]4[C:8]=3[N:7]=[CH:6][CH:5]=[CH:4]4)[CH2:20][CH2:19]2)=[O:31])[CH2:28][CH2:29]1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 67301190HCID 67301190, compound

Product 1

HCID 58368596HCID 58368596, compoundYield 67.7%

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 1-acetylpiperidine-4-carbonyl chloride (0.029 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 (eluting with 0 to 5% methanol in dichloromethane) to give the desired product (30 mg, 65%). LCMS calculated for C23H28ClN4O3 (M+H)+: m/z=443.2; Found: 443.2.

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-6e998351df8640ecbaaf24ef375b0c4e
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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