1,2-Ethanediamine, N1,N1,N2-trimethyl- → HCID 178493459、化合物

HRID 1189905

反応式

HRID 1189905 の反応式
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:15]([C:17]1[N:18]=[C:19]([NH:22][C:23]([C:25]2[C:26]3[N:27]=[CH:28][CH:29]=[N:30][C:31]=3[C:32]([C:35]3[C:40]([Cl:41])=[C:39]([O:42][CH3:43])[CH:38]=[C:37]([O:44][CH3:45])[C:36]=3[Cl:46])=[CH:33][CH:34]=2)=[O:24])[NH:20][CH:21]=1)=O.[CH3:47][N:48]([CH3:53])[CH2:49][CH2:50][NH:51][CH3:52]>C(Cl)Cl.C(Cl)Cl.O>[CH3:47][N:48]([CH3:53])[CH2:49][CH2:50][N:51]([CH2:15][C:17]1[N:18]=[C:19]([NH:22][C:23]([C:25]2[C:26]3[N:27]=[CH:28][CH:29]=[N:30][C:31]=3[C:32]([C:35]3[C:36]([Cl:46])=[C:37]([O:44][CH3:45])[CH:38]=[C:39]([O:42][CH3:43])[C:40]=3[Cl:41])=[CH:33][CH:34]=2)=[O:24])[NH:20][CH:21]=1)[CH3:52]

参加物

6

反応物 3

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 5049666Sodium triacetoxyborohydrideHCID 178493464HCID 178493464、化合物

生成物 1

HCID 178493459HCID 178493459、化合物収率 59.5%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 21908982Water methylene chloride溶媒

実験手順

Sodium triacetoxyborohydride (168 mg, 0.794 mmol, 3 equiv) was added to a suspension of 8-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid (4-formyl-1H-imidazol-2-yl)-amide (125 mg, 0.265 mmol) (Example 179) and N,N,N′-trimethylethylenediamine (81 mg, 0.792 mmol, 3 equiv) in DCM (4 mL) at rt, under an argon atmosphere. The reaction mixture was stirred for 18 h at rt, diluted in DCM/H2O and extracted with DCM. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1) followed by trituration in Et2O to afford 88 mg of the title compound as a yellow solid: ES-MS: 558 [M+H]+; tR=3.14 min (System 1); TLC: Rf=0.05 (DCM/MeOH/NH3aq, 94:5:1).

後処理

  1. extractionextracted with DCM
  2. washThe organic phase was washed with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1)

出典と根拠

ORDレコード
ord-62ca144a742e4319895e26f9c739f45d
出典データセット
uspto-grants-2014_03
特許番号
US08674099B2

関連ノート

読み込み中…