1,1'-Carbonyl-di-(1,2,4-triazole) → HCID 131734789、化合物

HRID 1777973ノート

反応式

HRID 1777973 の反応式
N1([C:6](N2C=NC=N2)=[O:7])C=NC=N1.[NH2:13][C:14]1[CH:21]=[C:20]([NH:22][CH2:23][CH2:24][O:25][CH3:26])[C:17]([C:18]#[N:19])=[CH:16][N:15]=1.[CH3:27][O:28][CH:29]([O:57][CH3:58])[C:30]1[C:39]([CH2:40][N:41]2[CH2:46][CH2:45][N:44]([C:47]([O:49][CH2:50][CH2:51][Si:52]([CH3:55])([CH3:54])[CH3:53])=[O:48])[CH2:43][C:42]2=[O:56])=[CH:38][C:37]2[CH2:36][CH2:35][CH2:34][NH:33][C:32]=2[N:31]=1>CN(C=O)C>[C:18]([C:17]1[C:20]([NH:22][CH2:23][CH2:24][O:25][CH3:26])=[CH:21][C:14]([NH:13][C:6]([N:33]2[C:32]3[N:31]=[C:30]([CH:29]([O:28][CH3:27])[O:57][CH3:58])[C:39]([CH2:40][N:41]4[CH2:46][CH2:45][N:44]([C:47]([O:49][CH2:50][CH2:51][Si:52]([CH3:53])([CH3:55])[CH3:54])=[O:48])[CH2:43][C:42]4=[O:56])=[CH:38][C:37]=3[CH2:36][CH2:35][CH2:34]2)=[O:7])=[N:15][CH:16]=1)#[N:19]

参加物

5

反応物 3

HCID 43939611,1'-Carbonyl-di-(1,2,4-triazole)HCID 1180369516-Amino-4-((2-methoxyethyl)amino)nicotinonitrile2 回HCID 1317347902-(Trimethylsilyl)ethyl 4-((2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-3-oxopiperazine-1-carboxylate2 回

生成物 1

HCID 131734789HCID 131734789、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

A solution of di(1H-1,2,4-triazol-1-yl)methanone (2.78 g, 15.23 mmol) in DMF (15 ml) was added to 6-amino-4-((2-methoxyethyl)amino)nicotinonitrile (intermediate 75, 2.96 g, 15.23 mmol) in anhydrous DMF (15 ml) at 0° C. After stirring for 2.5 h at room temperature a solution of 2-(trimethylsilyl)ethyl 4-((2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-3-oxopiperazine-1-carboxylate (intermediate 123, 2.83 g, 6.09 mmol) in DMF (20 ml) was added. The reaction mixture was stirred for 17.5 h at room temperature, then partitioned between saturated aqueous NaHCO3 solution and EtOAc, the EtOAc phase washed with brine, dried over MgSO4 and evaporated. The residue was applied to a RediSep® silica column and purified by normal phase chromatography, eluting with EtOAc then a gradient from hexane to 50% EtOAc in hexane. Product containing fractions were combined and evaporated to give the title compound as a clear pale yellow oil. (UPLC-MS 7) tR 1.28; ESI-MS 683.5 [M+H]+.

後処理

  1. additionwas added
  2. custompartitioned between saturated aqueous NaHCO3 solution and EtOAc
  3. washthe EtOAc phase washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. custompurified by normal phase chromatography
  7. washeluting with EtOAc
  8. additionProduct containing fractions
  9. customevaporated

出典と根拠

ORDレコード
ord-d114627c980d436a8946ffb7dfffee69
出典データセット
uspto-grants-2016_02
特許番号
US09266883B2

反応ノート

読み込み中…