Benzoyl chloride → HCID 58368468, compound

HRID 1192665Notes

Reaction equation

HRID 1192665 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](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>C(Cl)Cl>[C:21]([N:18]1[CH2:17][CH2:16][N:15]([C:9]2[C:10]([C:12](=[O:14])[CH3:13])=[CH:11][C:2]([Cl:1])=[C:3]3[C:8]=2[N:7]=[CH:6][CH:5]=[CH:4]3)[CH2:20][CH2:19]1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 67301190HCID 67301190, compound

Product 1

HCID 58368468HCID 58368468, compoundYield 129.5%

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 benzoyl chloride (0.018 mL, 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 and concentrated. The resulting residue was purified on silica gel (eluting with 0 to 5% MeOH in dichloromthane) to give the desired product (51 mg). LCMS calculated for C22H21ClN3O2 (M+H)+: m/z=394.1; Found: 394.0.

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% MeOH in dichloromthane)

Sources & evidence

ORD record
ord-dfe96d91ef2741d2811b83c3f4c83b82
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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