1,1'-Carbonyldiimidazole → 2-(2-(3-(Trifluoromethyl)-4,5,6,7-tetrahydroindazole-1-yl)acetamido)thiophene-3-carboxamide

HRID 1162748

반응식

HRID 1162748 반응식
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8].[F:10][C:11]([F:26])([F:25])[C:12]1[C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[N:14]([CH2:21][C:22](O)=[O:23])[N:13]=1.C(N1C=CN=C1)(N1C=CN=C1)=O>C(Cl)Cl.CN(C=O)C>[F:26][C:11]([F:10])([F:25])[C:12]1[C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[N:14]([CH2:21][C:22]([NH:1][C:2]2[S:3][CH:4]=[CH:5][C:6]=2[C:7]([NH2:9])=[O:8])=[O:23])[N:13]=1

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 6994952-Aminothiophene-3-carboxamideHCID 788039[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]acetic acid

생성물 1

HCID 529415022-(2-(3-(Trifluoromethyl)-4,5,6,7-tetrahydroindazole-1-yl)acetamido)thiophene-3-carboxamide수율 2%

시약·촉매·용매 1

HCID 22350042dichloromethane N,N-dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

2-aminothiophene-3-carboxamide (23 mg, 0.16 mmol) and 2-(3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole-1-yl)acetic acid (40 mg, 0.16 mmol) were dissolved in DCM/DMF (2 mL/50 μL) and polymer supported carbonyldiimidazole (264 mg, 1.2 mmol/g, 0.32 mmol) added. The reaction mixture was heated at 120° C. for 10 min in a Biotage SmithCreator microwave. The reaction mixture was filtered washing with MeOH (10 mL), EtOAc (10 mL), and MeCN (10 mL). The filtrate was concentrated in vacuo to give a yellow gum. Purification by preparative reverse phase HPLC gave desired product (1 mg, 2%).

후처리

  1. additionadded
  2. filtrationThe reaction mixture was filtered
  3. washwashing with MeOH (10 mL), EtOAc (10 mL), and MeCN (10 mL)
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give a yellow gum
  6. customPurification by preparative reverse phase HPLC

출처 및 근거

ORD 기록
ord-31b1677b6eee4b349fa72a597452b90c
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820707B2

연결된 노트

불러오는 중…