1,1'-Carbonyldiimidazole → 2-(3-(Trifluoromethyl)-4,5-dihydroindazole-1-yl)acetamido-4,5,6,7-tetrahydrothieno[2,3-c]pyran-3-carboxamide

HRID 1162746

反応式

HRID 1162746 の反応式
[NH2:1][C:2]1[S:10][C:5]2[CH2:6][O:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:11]([NH2:13])=[O:12].[F:14][C:15]([F:30])([F:29])[C:16]1[C:24]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=2[N:18]([CH2:25][C:26](O)=[O:27])[N:17]=1.C(N1C=CN=C1)(N1C=CN=C1)=O>C(Cl)Cl.CN(C=O)C>[F:30][C:15]([F:14])([F:29])[C:16]1[C:24]2[CH2:23][CH2:22][CH:21]=[CH:20][C:19]=2[N:18]([CH2:25][C:26]([NH:1][C:2]2[S:10][C:5]3[CH2:6][O:7][CH2:8][CH2:9][C:4]=3[C:3]=2[C:11]([NH2:13])=[O:12])=[O:27])[N:17]=1

参加物

5

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 788039[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]acetic acidHCID 436087732-amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxamide

生成物 1

HCID 249674202-(3-(Trifluoromethyl)-4,5-dihydroindazole-1-yl)acetamido-4,5,6,7-tetrahydrothieno[2,3-c]pyran-3-carboxamide収率 9%

試薬・触媒・溶媒 1

HCID 22350042dichloromethane N,N-dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

2-amino-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxamide (40 mg, 0.20 mmol) and 2-(3-(trifluoromethyl)-4,5,6,7-tetrahydroindazole-1-yl)acetic acid (50 mg, 0.20 mmol) were dissolved in DCM/DMF (3 mL/50 μL) and polymer supported carbonyldiimidazole (330 mg, 1.2 mmol/g, 0.396 mmol) added. The reaction mixture was heated at 120° C. for 10 min in the 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 as a white solid (7.6 mg, 0.018 mmol, 9%).

後処理

  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

出典と根拠

ORDレコード
ord-d35ec981d3be486f8f9b94200c0124db
出典データセット
uspto-grants-2010_10
特許番号
US07820707B2

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