1-Hydroxybenzotriazole → HCID 59714992, compound

HRID 2223897Notes

Reaction equation

HRID 2223897 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([N:17]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][N:26]=2)[C:18]([C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)=[O:19])[CH2:13][CH2:12]1.[CH:32]1([CH:38](C)[C:39](O)=[O:40])CCCCC1.ON1[C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=2N=N1.Cl.C(N=C=NCCCN(C)C)C>ClCCl.C(Cl)(Cl)Cl>[CH:47]1([CH2:32][CH2:38][C:39]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([N:17]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][N:26]=3)[C:18]([C:20]3[O:21][CH:22]=[CH:23][CH:24]=3)=[O:19])[CH2:13][CH2:12]2)=[O:40])[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 998162-Cyclohexylpropionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10180311HCID 10180311, compound

Product 1

HCID 59714992HCID 59714992, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[1-[3-(2-aminophenyl)propyl]piperidin-4-yl]-N-(5-methylpyridin-2-yl)-2-furancarboxamide (100 mg) and cyclohexylpropionic acid (49 mg) in dichloromethane (3 mL) were added 1-hydroxybenzotriazole (42 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (60 mg) under ice cooling. The solution was stirred at room temperature for 64 hours. Chloroform was then added to the solution and the solution was washed in turn with water and saturated aqueous sodium bicarbonate solution. The solution was dried over anhydrous sodium sulfate, and then, concentrated under reduced pressure. The residue was purified by chromatography (NH silica gel, hexane:ethyl acetate=1:2) to give the title compound (120 mg).

Workup

  1. washthe solution was washed in turn with water and saturated aqueous sodium bicarbonate solution
  2. dry with materialThe solution was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography (NH silica gel, hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-97772d4b11bc4a0ba32b83ddf38cfc55
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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