Triethylamine → HCID 58368436, compound

HRID 1192678Notes

Reaction equation

HRID 1192678 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.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=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:22]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=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 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 67301190HCID 67301190, compound

Product 1

HCID 58368436HCID 58368436, compoundYield 98.8%

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 nicotinoyl 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 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 (39 mg, 95%). 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-7bc1284da40b46c78b50a34e948510ae
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

Loading…