Triethylamine → 6-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]-N-[2-(2-thienyl)ethyl]nicotinamide

HRID 381383Notes

Reaction equation

HRID 381383 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.[S:42]1[CH:46]=[CH:45][CH:44]=[C:43]1[CH2:47][CH2:48][NH2:49]>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]([NH:49][CH2:48][CH2:47][C:43]4[S:42][CH:46]=[CH:45][CH:44]=4)=[O:32])=[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 8471Triethylamine2×HCID 62493Pivaloyl chlorideHCID 116521ThiopheneethanamineHCID 183628186-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid

Product 1

HCID 183628556-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]-N-[2-(2-thienyl)ethyl]nicotinamideYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

Triethylamine (0. 8 ml) was added to 6-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid (2g) in methylene chloride (30 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 for 1 hour. With the successive addition of triethylamine (0.9 ml) and 2-thiophenethylamine (0.75 g), the mixture was stirred at 5° C.˜10° C. for 2 hours. The solution was washed with an aqueous sodium bicarbonate and water. The separated organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The concentrated residue was treated with ether for crystallization. The solid, so obtained, was recrystallized with ethanol and hexane to give a desired compound of 1.92 g (yield: 74%).

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred at 5° C.˜10° C. for 2 hours
  3. washThe solution was washed with an aqueous sodium bicarbonate and water
  4. dry with materialThe separated organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionThe concentrated residue was treated with ether for crystallization
  7. customThe solid, so obtained
  8. customwas recrystallized with ethanol and hexane

Sources & evidence

ORD record
ord-4884cd17793d419096a507e3e8d4d7b5
Source dataset
uspto-grants-2001_10
Patent number
US06306860B1

Reaction notes

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