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

HRID 1455953노트

반응식

HRID 1455953 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8471Triethylamine용매

반응 조건

온도
5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2ecfc51f22fb4129aadd47bcba2c8270
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05843942

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