Dimethylcarbamoyl Chloride → HCID 58368647, compound

HRID 1192663Notes

Reaction equation

HRID 1192663 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][N:22]([CH3:26])[C:23](Cl)=[O:24].C(N(CC)CC)C>ClCCl>[C:12]([C:10]1[C:9]([N:15]2[CH2:16][CH2:17][N:18]([C:23]([N:22]([CH3:26])[CH3:21])=[O:24])[CH2:19][CH2:20]2)=[C:8]2[C:3]([CH:4]=[CH:5][CH:6]=[N:7]2)=[C:2]([Cl:1])[CH:11]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 67301190HCID 67301190, compound

Product 1

HCID 58368647HCID 58368647, compoundYield 74.8%

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 N,N-dimethylcarbamoyl chloride (0.014 mL, 0.16 mmol) and triethylamine (0.043 mL, 0.31 mmol) in methylene chloride (1.0 mL, 16 mmol) 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% MeOH in dichloromethane) to give the desired product (27 mg, 72%). LCMS calculated for C18H22ClN4O2 (M+H)+: m/z=361.1; Found: 361.0.

Workup

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

Sources & evidence

ORD record
ord-044e527e1f69423c95fc78e5bca554a4
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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