Heptanoic Acid → 4-[5-(4-Heptanoyl-piperazin-1-ylmethyl)-imidazol-1-ylmethyl]-benzonitrile

HRID 276789Notes

Reaction equation

HRID 276789 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH:9]2[CH2:14]C2NC=NC=2)=[CH:5][CH:4]=1)#[N:2].[C:22]([OH:30])(=O)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].O[N:32]1C2C=CC=CC=2N=N1.[CH2:41]([N:43]([CH2:46]C)CC)[CH3:42].Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[C:22]([N:43]1[CH2:46][CH2:12][N:11]([CH2:10][C:9]2[N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:21][CH:20]=3)[CH:13]=[N:32][CH:14]=2)[CH2:42][CH2:41]1)(=[O:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

8

Reactant 5

HCID 8094Heptanoic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 536553351-(4'-Cyanobenzyl)imidazol-5-ylmethyl piperazine

Product 1

HCID 98219494-[5-(4-Heptanoyl-piperazin-1-ylmethyl)-imidazol-1-ylmethyl]-benzonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4′-Cyanobenzyl)imidazol-5-ylmethyl piperazine, prepared as described in Example 1 (65 mg, 0.18 mmol), in 0.5 mL of dimethylformamide at room temperature was added heptanoic acid (0.028 mL, 0.2 mmol), 1-hydroxybenzotriazole (30 mg, 0.22 mmol), triethylamine (0.10 mL, 0.72 mmol), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (42 mg, 0.22 mmol). After sti!ting overnight, the solution was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution and brine, dried with sodium sulfate, filtered, and concentrated in vacuo. Purification by preparative HPLC was followed by conversion to the bis-hydrochloride salt by exposure of a dichloromethane solution of the product to excess ethereal HCl. Concentration in vacuo provided the titled product as a white powder (23 mg). MS: found: 394 (M+H+)

Workup

  1. washwashed with saturated sodium bicarbonate solution and brine
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by preparative HPLC
  6. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-5aa75ee985764e388cc94752066ba9ca
Source dataset
uspto-grants-2002_03
Patent number
US06355643B1

Reaction notes

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