Isopropylamine → HCID 499742, compound

HRID 381363Notes

Reaction equation

HRID 381363 reaction equation
C(N(CC)CC)C.[CH:8]([NH:11][C:12]1[C:13]([N:18]2[CH2:23][CH2:22][N:21]([C:24]([C:26]3[CH:34]=[CH:33][C:29]([C:30]([OH:32])=O)=[CH:28][N:27]=3)=[O:25])[CH2:20][CH2:19]2)=[N:14][CH:15]=[CH:16][CH:17]=1)([CH3:10])[CH3:9].C(Cl)(=O)C(C)(C)C.[CH:42]([NH2:45])([CH3:44])[CH3:43]>C(Cl)Cl>[CH:8]([NH:11][C:12]1[C:13]([N:18]2[CH2:19][CH2:20][N:21]([C:24]([C:26]3[CH:34]=[CH:33][C:29]([C:30](=[O:32])[NH:45][CH:42]([CH3:44])[CH3:43])=[CH:28][N:27]=3)=[O:25])[CH2:22][CH2:23]2)=[N:14][CH:15]=[CH:16][CH:17]=1)([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 8471Triethylamine2×HCID 62493Pivaloyl chlorideHCID 183628186-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid

Product 1

HCID 499742HCID 499742, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.6 ml) was added to 6-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid (4 g) in methylene chloride (50 ml) for dissolution and cooled. With the slow addition of pivaloyl chloride (1.4 ml) at 0° C.˜5° C., the mixture was stirred at 5 C for 1 hour. With the addition of triethylamine (1.7 ml) and isopropylamine (1.2 ml), the mixture was stirred at 10° C. for 2 hours. The solution was washed with aqueous sodium bicarbonate and water twice. The separated organic layer was dried over magnesium sulfate and concentrated under reduced pressure. Isopropanol (40 ml) was added to the concentrated residue, stirred and filtered. The solid was recrystallized with ethyl acetate and ether to give a desired compound of 3.6 g (yield: 81%).

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred at 10° C. for 2 hours
  3. washThe solution was washed with aqueous sodium bicarbonate and water twice
  4. dry with materialThe separated organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionIsopropanol (40 ml) was added to the concentrated residue
  7. stirringstirred
  8. filtrationfiltered
  9. customThe solid was recrystallized with ethyl acetate and ether

Sources & evidence

ORD record
ord-c9a3b9aba5554e0aaf0118750c8bf356
Source dataset
uspto-grants-2001_10
Patent number
US06306860B1

Reaction notes

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