3,5-Dimethylpyrazole-1-carboxamidine → N-(3-cyanophenyl)-N'-(1-amidinopiperidin-4-yl)cycloheptylurea

HRID 582565

反応式

HRID 582565 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([N:9]([CH:19]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:10]([NH:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].CC1C=C(C)[N:29]([C:33](N)=[NH:34])N=1>N1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([N:9]([CH:19]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:10]([NH:12][CH:13]2[CH2:18][CH2:17][N:16]([C:33](=[NH:29])[NH2:34])[CH2:15][CH2:14]2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2]

参加物

4

反応物 2

HCID 975253,5-Dimethylpyrazole-1-carboxamidineHCID 54268872HCID 54268872、化合物

生成物 1

HCID 54155874N-(3-cyanophenyl)-N'-(1-amidinopiperidin-4-yl)cycloheptylurea収率 74.7%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
110 °C

実験手順

N-(3-Cyanophenyl)-N'-(piperidin-4-yl)cycloheptylurea (0.05 g, 0.126 mmol) was dissolved in pyridine (2 ml) and 3,5-dimethylpyrazole-1-carboxamidine (0.037 g, 0.188 mmol) was added under a nitrogen atmosphere. The reaction was heated to 110° C. for 6 h, then was allowed to cool and was concentrated to give a viscous amber oil. The product was purfied by HPLC on a Vydec® C-18 column eluting with solvent mixture A (acetonitrile:water:TFA 80:20:0.3) and solvent mixture B (water:TFA 99.7:0.3) using a gradient starting with A:B at 3:97 and changing to A:B at 70:30 over 15 min. The product eluted at 13.8 minutes was concentrated to give N-(3-cyanophenyl)-N'-(1-amidinopiperidin-4-yl)cycloheptylurea as an amorphous solid (0.036 g); LRMS (M+H)+ m/z 341.

後処理

  1. temperatureto cool
  2. concentrationwas concentrated
  3. customto give a viscous amber oil
  4. washeluting with solvent mixture A (acetonitrile:water:TFA 80:20:0.3) and solvent mixture B (water:TFA 99.7:0.3)
  5. customover 15 min
  6. washThe product eluted at 13.8 minutes
  7. concentrationwas concentrated

出典と根拠

ORDレコード
ord-316411f4a0204f9fa3b97b57b853aed9
出典データセット
uspto-grants-1999_07
特許番号
US05925635

関連ノート

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