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

HRID 276789ノート

反応式

HRID 276789 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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+)

後処理

  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

出典と根拠

ORDレコード
ord-5aa75ee985764e388cc94752066ba9ca
出典データセット
uspto-grants-2002_03
特許番号
US06355643B1

反応ノート

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