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

HRID 276789노트

반응식

HRID 276789 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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+)

후처리

  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

출처 및 근거

ORD 기록
ord-5aa75ee985764e388cc94752066ba9ca
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355643B1

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