Isopropylamine → 5-(n-Isopropylcarbamoyl)-2-[1-(3-nitro-2-pyridyl)piperazin-4-yl-carbonyl]pyridine

HRID 381365Notes

Reaction equation

HRID 381365 reaction equation
[N+:1]([C:4]1[C:5]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][N:19]=3)=[O:17])[CH2:12][CH2:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(Cl)(=O)C(C)(C)C.[CH:34]([N:37](CC)C(C)C)([CH3:36])[CH3:35].C(N)(C)C>C(Cl)Cl.C(N(CC)CC)C>[CH:34]([NH:37][C:22]([C:21]1[CH:25]=[CH:26][C:18]([C:16]([N:13]2[CH2:12][CH2:11][N:10]([C:5]3[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][N:6]=3)[CH2:15][CH2:14]2)=[O:17])=[N:19][CH:20]=1)=[O:24])([CH3:36])[CH3:35]

Participants

7

Reactant 4

HCID 6363IsopropylamineHCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 183628396-[1-(3-Nitro-2-pyridyl)piperazin-4-yl-carbonyl]nicotinic acid

Product 1

HCID 183628135-(n-Isopropylcarbamoyl)-2-[1-(3-nitro-2-pyridyl)piperazin-4-yl-carbonyl]pyridineYield 78%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Triethylamine (0.85 ml) was added to 6-[1-(3-nitro-2-pyridyl)piperazin-4-yl-carbonyl]nicotinic acid (2 g) in methylene chloride (25 ml) for dissolution and cooled. With the slow addition of pivaloyl chloride (0.7 ml) at 0° C.˜5° C., the mixture was stirred at 5° C.˜10° C. for 2 hours. With the addition of N,N-diisopropylethylamine (1.1 ml) and isopropylamine (0.55 ml), the mixture was stirred at 10° C.˜15° C. for 3 hours. The reaction mixture was washed with an aqueous sodium bicarbonate and water twice. The separated organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in chloroform (15 ml) and with the slow addition of ether, crystals were precipitated. For 2-hours stirring, the precipitate was filtered, washed (ether) and dried to give a desired compound of 1.74 g (yield: 78%).

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred at 10° C.˜15° C. for 3 hours
  3. washThe reaction mixture was washed with an aqueous sodium bicarbonate and water twice
  4. dry with materialThe separated organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in chloroform (15 ml) and with the slow addition of ether, crystals
  7. customwere precipitated
  8. stirringFor 2-hours stirring
  9. filtrationthe precipitate was filtered
  10. washwashed (ether)
  11. customdried

Sources & evidence

ORD record
ord-cb25f6fce5564821a8203a3b17e8b609
Source dataset
uspto-grants-2001_10
Patent number
US06306860B1

Reaction notes

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