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

Reaktionsgleichung

[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

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

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%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-d35ec981d3be486f8f9b94200c0124db
Quelldatensatz: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07820707B2

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