Oxalyl chloride → 1-(4-Dimethylaminopiperidin-1-yl)-2-thiophen-2-yl-ethane-1,2-dione

HRID 220330

반응식

HRID 220330 반응식
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:10])[C:7]([OH:9])=O.C(Cl)(=O)C(Cl)=O.[CH3:17][N:18]([CH3:25])[CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1.CN(C=O)C>[CH3:17][N:18]([CH3:25])[CH:19]1[CH2:24][CH2:23][N:22]([C:7](=[O:9])[C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:21][CH2:20]1

참가 물질

8

반응물 4

HCID 65578Oxalyl chlorideHCID 776942-Thiopheneglyoxylic acidHCID 81531DiisopropylethylamineHCID 417391N,N-Dimethylpiperidin-4-amine

생성물 1

HCID 598285231-(4-Dimethylaminopiperidin-1-yl)-2-thiophen-2-yl-ethane-1,2-dione수율 98.4%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매3회

실험 절차

2-Thiopheneglyoxylic acid (300 mg, 1.9 mmol) was dissolved in 10 mL of methylene chloride. A 2.0 M solution of oxalyl chloride in methylene chloride (1.1 mL, 2.1 mmol) was then added, followed by 10 μL of DMF. The resulting solution was stirred at room temperature for 1 hour, then a solution of dimethylpiperidin-4-ylamine (271 mg, 2.1 mmol) and DIPEA (1.0 mL, 5.8 mmol) in 2 mL of methylene chloride was added. 4-Dimethylaminopyridine (12 mg, 96 μmol) was then added and the resulting mixture was stirred at room temperature for 2 hours. The mixture was then extracted with a saturated sodium bicarbonate solution, and the organic layer was dried over Na2SO4 and concentrated to yield the crude intermediate (4a) (498 mg), which was used in the next step without further purification.

후처리

  1. stirringthe resulting mixture was stirred at room temperature for 2 hours
  2. extractionThe mixture was then extracted with a saturated sodium bicarbonate solution
  3. dry with materialthe organic layer was dried over Na2SO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-41b1e7b8df8c44c797c03d084b8e46d5
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202891B2

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