Dimethylformamide → 6-amino-5-cyano-N-((1-((2-(pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methyl)imidazo[1,2-a]pyridine-8-carboxamide

HRID 2407743ノート

反応式

HRID 2407743 の反応式
[N:1]1(O)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=N1.[CH2:11]([N:13](CC)CC)[CH3:12].C([N:20]=C=NCCCN(C)C)C.Cl.Cl.Cl.[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:38]1[S:39][C:40]([CH2:43][N:44]2[CH2:49][CH2:48][CH:47]([CH2:50][NH2:51])[CH2:46][CH2:45]2)=[CH:41][N:42]=1.CN(C)[CH:54]=[O:55]>C(=O)([O-])O.[Na+]>[NH2:20][C:8]1[CH:7]=[C:6]([C:54]([NH:51][CH2:50][CH:47]2[CH2:46][CH2:45][N:44]([CH2:43][C:40]3[S:39][C:38]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=4)=[N:42][CH:41]=3)[CH2:49][CH2:48]2)=[O:55])[C:5]2[N:1]([CH:12]=[CH:11][N:13]=2)[C:9]=1[C:4]#[N:3]

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 8471Triethylamine2 回HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-Hydroxybenzotriazole2 回HCID 66989375(1-((2-(Pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methanamine Trihydrochloride2 回

生成物 1

HCID 585041036-amino-5-cyano-N-((1-((2-(pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methyl)imidazo[1,2-a]pyridine-8-carboxamide

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
40 °C

実験手順

This material was then combined with 1H-benzo[d][1,2,3]triazol-1-ol (0.012 g), and triethylamine (0.0613 mL) in N,N-dimethylformamide (0.5 mL). 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (0.0145 g) was then added to the reaction mixture. After stirring for 30 minutes, the compound prepared in Example 214 (0.030 g) was added to the reaction mixture. The reaction mixture was allowed to stir at room temperature for 3 hours. Equivalent amounts of 1H-benzo[d][1,2,3]triazol-1-ol, triethylamine, and the compound prepared in Example 214 were added to the reaction mixture, and then heated at 40° C. for 17 hours. The reaction mixture was diluted with saturated sodium hydrogen carbonate aqueous solution and extracted with ethyl acetate. The combined organics were then washed with water and brine, dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=19:1) to obtain the title compound (0.0085 g) having the following physical data.

後処理

  1. stirringto stir at room temperature for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organics were then washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=19:1)

出典と根拠

ORDレコード
ord-d44912bbdfa247039335da765ad28bd1
出典データセット
uspto-grants-2014_08
特許番号
US08809538B2

反応ノート

読み込み中…