Ethyl Acetate → HCID 89922410、化合物

HRID 921868ノート

反応式

HRID 921868 の反応式
[Cl:1][C:2]1[C:9]([N+:10]([O-])=O)=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][C:14]1=[O:20].[Cl-].[NH4+].C(=O)(O)[O-].[Na+].CCOC(C)=O>CO.[Zn]>[NH2:10][C:9]1[CH:8]=[C:5]([CH:4]=[C:3]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][C:14]2=[O:20])[C:2]=1[Cl:1])[C:6]#[N:7]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 899234104-Chloro-3-(4-methyl-2-oxo-1-piperazinyl)-5-nitrobenzonitrile

生成物 1

HCID 89922410HCID 89922410、化合物収率 77.8%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

実験手順

To a solution of 4-chloro-3-(4-methyl-2-oxopiperazin-1-yl)-5-nitrobenzonitrile (40 mg, 0.136 mmol) in MeOH (4 mL) was added ammonium chloride (218 mg, 4.07 mmol) and zinc (133 mg, 2.036 mmol) (in two portions, after the first portion, reaction was not complete). After stirring at room temperature for 12 h. LC-MS indicated completion. Then 5 mL of saturated aqueous sodium bicarbonate solution was added followed by 10 mL of EtOAc. The mixture was filtered through a pad of Celite and the filter cake was washed EtOAc. The solvent from the filtrate was evaporated. Purification via flash chromatography (0-10% MeOH in DCM, 24 g) gave 3-amino-4-chloro-5-(4-methyl-2-oxopiperazin-1-yl)benzonitrile (28 mg) as an off-white solid.

後処理

  1. customafter the first portion, reaction
  2. filtrationThe mixture was filtered through a pad of Celite
  3. washthe filter cake was washed EtOAc
  4. customThe solvent from the filtrate was evaporated
  5. customPurification via flash chromatography (0-10% MeOH in DCM, 24 g)

出典と根拠

ORDレコード
ord-fc85f0be09a744b1904f4b882e4cf220
出典データセット
uspto-grants-2016_03
特許番号
US09273057B2

反応ノート

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