Dicyclohexylcarbodiimide → HCID 18362799, compound

HRID 381382Notes

Reaction equation

HRID 381382 reaction equation
[CH:1]([NH:4][C:5]1[C:6]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][N:20]=3)=[O:18])[CH2:13][CH2:12]2)=[N:7][CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[NH2:53][CH2:54][C:55]1[CH:56]=[N:57][CH:58]=[CH:59][CH:60]=1>C(Cl)Cl.O1CCCC1>[CH:1]([NH:4][C:5]1[C:6]([N:11]2[CH2:12][CH2:13][N:14]([C:17]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([NH:53][CH2:54][C:55]4[CH:56]=[N:57][CH:58]=[CH:59][CH:60]=4)=[O:25])=[CH:21][N:20]=3)=[O:18])[CH2:15][CH2:16]2)=[N:7][CH:8]=[CH:9][CH:10]=1)([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 310183-PyridinemethanamineHCID 757711-HydroxybenzotriazoleHCID 183628186-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid

Product 1

HCID 18362799HCID 18362799, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

6-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid (2 g) was added to a co-solvent of tetrahydrofuran (30 ml) and methylene chloride (30 ml) and with the successive addition of 1,3-dicyclohexylcarbodimide (2.4 g) and 1-hydroxybenzotriazole (0.85 g) at 15° C.˜20° C., the mixture was reacted at the same temperature for 2 hours. With the addition of 3-(aminomethyl)pyridine (0.65 g) at 20° C., the reaction mixture was stirred at 20° C.˜25° C. for 2 hours. With the addition of methylene chloride (60 ml). The mixture was washed with water 3 times, dried over magnesium sulfate and concentrated under reduced pressure. The concentrated residue was chromatographed on column (hexane/chloroform/ethanol=5/2/1, v/v/v). The purified solution was concentrated under reduced pressure, and then, the residue was treated with ether for crystallization to give a desired compound of 1.87 g (yield: 75%).

Workup

  1. customthe mixture was reacted at the same temperature for 2 hours
  2. washThe mixture was washed with water 3 times
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrated residue was chromatographed on column (hexane/chloroform/ethanol=5/2/1, v/v/v)
  6. concentrationThe purified solution was concentrated under reduced pressure
  7. additionthe residue was treated with ether for crystallization

Sources & evidence

ORD record
ord-7fa8215784324c079fd111513df887ab
Source dataset
uspto-grants-2001_10
Patent number
US06306860B1

Reaction notes

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