1,1'-Thiocarbonyldi-2(1H)-pyridone → 2-(4-(4-(2-(5-Cyclobutyl-1,3,4-thiadiazol-2-ylamino)pyrimidin-5-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid

HRID 881722노트

반응식

HRID 881722 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]34[CH2:21][CH2:20][C:17]([CH2:22][C:23]([O:25]C)=[O:24])([CH2:18][CH2:19]3)[O:16][CH2:15]4)=[CH:10][CH:9]=2)=[CH:4][N:3]=1.[C:27](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:28].[CH:43]1([C:47]([NH:49][NH2:50])=O)[CH2:46][CH2:45][CH2:44]1>ClCCl>[CH:43]1([C:47]2[S:28][C:27]([NH:1][C:2]3[N:7]=[CH:6][C:5]([C:8]4[CH:9]=[CH:10][C:11]([C:14]56[CH2:21][CH2:20][C:17]([CH2:22][C:23]([OH:25])=[O:24])([CH2:18][CH2:19]5)[O:16][CH2:15]6)=[CH:12][CH:13]=4)=[CH:4][N:3]=3)=[N:50][N:49]=2)[CH2:46][CH2:45][CH2:44]1

참가 물질

5

반응물 3

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 969366CyclobutanecarbohydrazideHCID 86700829Methyl 2-(4-(4-(2-aminopyrimidin-5-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

생성물 1

HCID 721883882-(4-(4-(2-(5-Cyclobutyl-1,3,4-thiadiazol-2-ylamino)pyrimidin-5-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid수율 83%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

To a reaction vial containing methyl 2-(4-(4-(2-aminopyrimidin-5-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (40 mg, 0.11 mmol) was added dichloromethane (1 ml) at room temperature. 1,1′-thiocarbonyldipyridin-2(1H)-one (29 mg, 0.12 mmol) was added and the resulting mixture was heated to 50° C. for overnight. The mixture was cool down to room temperature and cyclobutanecarbohydrazide (19 mg, 0.17 mmol) was then added and stirred at room temperature for another hour. The content was then concentrated to dryness and the resulting residue was taken up in MeOH to form a nice slurry. The slurry was filtered and washed with small amount of MeOH to afford the title compound as off-white solid after drying (48 mg, 83% yield). LC/MS, ESI-MS(+): 510.4, RT: 1.26 (Condition E)

후처리

  1. temperatureThe mixture was cool down to room temperature
  2. concentrationThe content was then concentrated to dryness
  3. customto form a nice slurry
  4. filtrationThe slurry was filtered
  5. washwashed with small amount of MeOH

출처 및 근거

ORD 기록
ord-45297966a341431fa1d42fbd9adc6ee5
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993619B2

반응 노트

불러오는 중…