Triethylamine → HCID 58368659, compound

HRID 1192676Notes

Reaction equation

HRID 1192676 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.Cl.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28](Cl)=[O:29].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:28]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][N:22]=3)=[O:29])[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 135033Picolinoyl Chloride HydrochlorideHCID 67301190HCID 67301190, compound

Product 1

HCID 58368659HCID 58368659, compoundYield 38%

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 pyridine-2-carbonyl chloride hydrochloride (0.028 g, 0.16 mmol) and triethylamine (0.058 mL, 0.41 mmol) in methylene chloride (1.0 mL) at room temperature and stirred overnight. 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 (15 mg, 37%). LCMS calculated for C21H20ClN4O2 (M+H)+: m/z=395.1; Found: 395.1.

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-75f4259891c94e58b62d212fec4efc14
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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