Triethylamine → HCID 58368646, compound

HRID 1192656Notes

Reaction equation

HRID 1192656 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:24](Cl)=[O:25])[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:24]([CH:21]3[CH2:23][CH2:22]3)=[O:25])[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 77637Cyclopropanecarbonyl chlorideHCID 67301190HCID 67301190, compound

Product 1

HCID 58368646HCID 58368646, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(5-chloro-8-piperazin-1-ylquinolin-7-yl)ethanone (0.063 g, 0.22 mmol) was combined with cyclopropanecarbonyl chloride (0.029 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 concentrated. The resulting residue was purified on silica gel (eluting with 0 to 5% methanol in dichloromthane) to give the desired product (21 mg, 27%). LCMS calculated for C19H21ClN3O2 (M+H)+: m/z=358.1; Found: 358.0.

Workup

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

Sources & evidence

ORD record
ord-bdf4fe57711b46bb85e407c07e609b1d
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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