Ethyl Acetate → HCID 89922410, 화합물

HRID 921868노트

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HRID 921868 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 89922410HCID 89922410, 화합물수율 77.8%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-fc85f0be09a744b1904f4b882e4cf220
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273057B2

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