Potassium ethyl malonate → ethyl [6-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]pyridazin-3-ylcarbonyl]acetate

HRID 1455953ノート

反応式

HRID 1455953 の反応式
[CH2:1]([O:8][C:9]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:10]=1[CH2:11][N:12]([C:15]1[N:20]=[N:19][C:18]([C:21]([OH:23])=O)=[CH:17][CH:16]=1)[CH2:13][CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.[C:41]([O:47][CH2:48][CH3:49])(=[O:46])[CH2:42]C([O-])=O.[K+].[Cl-].[Mg+2].[Cl-]>C(#N)C.C(N(CC)CC)C>[CH2:1]([O:8][C:9]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:10]=1[CH2:11][N:12]([C:15]1[N:20]=[N:19][C:18]([C:21]([CH2:42][C:41]([O:47][CH2:48][CH3:49])=[O:46])=[O:23])=[CH:17][CH:16]=1)[CH2:13][CH3:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 3446434Potassium ethyl malonateHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 5360315Magnesium ChlorideHCID 98461706-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]pyridazine-3-carboxylic acid

生成物 1

HCID 53869694ethyl [6-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]pyridazin-3-ylcarbonyl]acetate収率 86.3%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8471Triethylamine溶媒

反応条件

温度
5 °C

実験手順

A mixture of 6-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]pyridazine-3-carboxylic acid (12.5 g) and carbonyl di-imidazole (6.0 g) was heated at 5° C. for 1 hour. Separately, a mixture of potassium ethyl malonate (7.0 g), triethylamine (8.0 ml) and anhydrous magnesium chloride (5.0 g) in acetonitrile (200 ml) was stirred at ambient temperature for 2 hours. The two mixtures were combined and stirred for 18 hours at ambient temperature, then at reflux for 1 hour. The solvents were evaporated, and the residue partitioned between dichloromethane and 2N HCl. The organic solution was dried (MgSO4) and evaporated. The resulting residue was purified by flash chromatography, eluting with diethyl ether, to give ethyl [6-[N-(2-benzyloxy-5-bromobenzyl)-N-ethylamino]pyridazin-3-ylcarbonyl]acetate (12.5 g) as a yellow gum.

後処理

  1. stirringstirred for 18 hours at ambient temperature
  2. temperatureat reflux for 1 hour
  3. customThe solvents were evaporated
  4. customthe residue partitioned between dichloromethane and 2N HCl
  5. dry with materialThe organic solution was dried (MgSO4)
  6. customevaporated
  7. customThe resulting residue was purified by flash chromatography
  8. washeluting with diethyl ether

出典と根拠

ORDレコード
ord-2ecfc51f22fb4129aadd47bcba2c8270
出典データセット
uspto-grants-1998_12
特許番号
US05843942

反応ノート

読み込み中…