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 881722ノート

反応式

HRID 881722 の反応式
[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

参加物

5

反応物 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

生成物 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 acid収率 83%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-45297966a341431fa1d42fbd9adc6ee5
出典データセット
uspto-grants-2015_03
特許番号
US08993619B2

反応ノート

読み込み中…