Dicyclohexylcarbodiimide → 3-cyclopentyl-2-(3,4-dichlorophenyl)-N-[1,2,4]triazin-3-yl-propionamide

HRID 398561

반응식

HRID 398561 반응식
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:34][C:35]1[N:36]=[N:37][CH:38]=[CH:39][N:40]=1>N1C=CC=CC=1>[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C:8]([NH:34][C:35]2[N:36]=[N:37][CH:38]=[CH:39][N:40]=2)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 707153-Amino-1,2,4-triazineHCID 27627253-cyclopentyl-2-(3,4-dichlorophenyl)propanoic Acid

생성물 1

HCID 223152313-cyclopentyl-2-(3,4-dichlorophenyl)-N-[1,2,4]triazin-3-yl-propionamide수율 8%

시약·촉매·용매 1

HCID 1049Pyridine용매2회

반응 조건

온도
25 °C

실험 절차

A solution of 3-cyclopentyl-2-(3,4-dichlorophenyl)-propionic acid (prepared as in Example 38A, 400 mg, 1.40 mmol) in dry pyridine (5 mL) was treated with 1,3-dicyclohexylcarbodiimide (316 mg, 1.53 mmol). The reaction mixture was stirred at 25° C. for 3.5 h and then treated with 3-amino-1,2,4-triazine (296 mg, 3.08 mmol) and an additional amount of pyridine (1 mL). The reaction mixture was warmed at 100° C. for 20 h. The reaction mixture was concentrated in vacuo to remove pyridine. The resulting residue was diluted with ethyl acetate then filtered. The filtrate was washed with a 1N aqueous hydrochloric acid solution and washed with water. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/1 ethyl acetate/hexanes) afforded 3-cyclopentyl-2-(3,4-dichlorophenyl)-N-[1,2,4]triazin-3-yl-propionamide (40.9 mg, 8%) as a yellow-orange solid: mp 81-83° C.; EI-HRMS m/e calcd for C17H18Cl2N4O (M+) 364.0858, found 364.0857.

후처리

  1. temperatureThe reaction mixture was warmed at 100° C. for 20 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto remove pyridine
  4. additionThe resulting residue was diluted with ethyl acetate
  5. filtrationthen filtered
  6. washThe filtrate was washed with a 1N aqueous hydrochloric acid solution
  7. washwashed with water
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-559d42a266db4746b25b9f7f0b0516e8
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610846B1

연결된 노트

불러오는 중…