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1,1'-Carbonyldiimidazole → 4-(3,3-Dimethyl-butyl)-piperazine-1-carboxylic Acid [4-(3,6-dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-cyclohexylmethyl]-amide

HRID 220810
ノート
印刷プレビュー

反応式

HRID 220810 の反応式
CCN(C(C)C)C(C)C.[C:10](N1C=CN=C1)(N1C=CN=C1)=[O:11].Cl.[NH2:23][CH2:24][CH:25]1[CH2:30][CH2:29][CH:28]([C:31]([N:33]2[CH2:42][C:41]3[CH:40]=[N:39][N:38]([CH3:43])[C:37]=3[NH:36][C:35]3[CH:44]=[C:45]([CH3:48])[CH:46]=[CH:47][C:34]2=3)=[O:32])[CH2:27][CH2:26]1.Cl.Cl.[CH3:51][C:52]([CH3:62])([CH3:61])[CH2:53][CH2:54][N:55]1[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]1>CN(C=O)C.CCOC(C)=O>[CH3:43][N:38]1[C:37]2[NH:36][C:35]3[CH:44]=[C:45]([CH3:48])[CH:46]=[CH:47][C:34]=3[N:33]([C:31]([CH:28]3[CH2:29][CH2:30][CH:25]([CH2:24][NH:23][C:10]([N:58]4[CH2:57][CH2:56][N:55]([CH2:54][CH2:53][C:52]([CH3:62])([CH3:61])[CH3:51])[CH2:60][CH2:59]4)=[O:11])[CH2:26][CH2:27]3)=[O:32])[CH2:42][C:41]=2[CH:40]=[N:39]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 670538001-(3,3-Dimethyl-butyl)-piperazine dihydrochlorideHCID 136346633(4-Aminomethyl-cyclohexyl)-(3,6-dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone hydrochloride

生成物 1

HCID 135475995
4-(3,3-Dimethyl-butyl)-piperazine-1-carboxylic Acid [4-(3,6-dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-cyclohexylmethyl]-amide
収率 29.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

DIEA (0.30 ml, 1.7 mmol) and 1,1′-carbonyldiimidazole (39 mg, 0.24 mmol) were added to a solution of (4-aminomethyl-cyclohexyl)-(3,6-dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone hydro-chloride (Compound number 149) (78 mg, 0.20 mmol) in DMF (4.0 ml) and the mixture was stirred at room temperature for 2 h. 1-(3,3-Dimethyl-butyl)-piperazine dihydrochloride from Example E4 (56 mg, 0.23 mmol) was added and the mixture was stirred at room temperature for 18 h. The mixture was diluted with EtOAc, washed with brine, dried and concentrated in vacuo. The residue was purified by preparative HPLC (eluant; 10% methanol:90% di-chloromethane) to give a white solid identified as the title compound (32 mg, 29%).

後処理

  1. stirringthe mixture was stirred at room temperature for 18 h
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC (eluant; 10% methanol:90% di-chloromethane)
  6. customto give a white solid

出典と根拠

ORDレコード
ord-1ee9691b6de249228c0463692443256e
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08202858B2

反応ノート

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