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Diisopropylethylamine → 2-Methyl-6-{[2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy}benzo[b]thiophene-3-carboxylic acid cyclopropylamide

HRID 985321
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 985321
[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[N:22]([CH3:26])[CH:23]=[CH:24][N:25]=5)[S:20][C:13]=34)[CH:9]=[CH:10][C:4]=2[C:3]=1[C:27]([OH:29])=O.C([N:33](CC)[CH:34]([CH3:36])[CH3:35])(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:34]1([NH:33][C:27]([C:3]2[C:4]3[CH:10]=[CH:9][C:8]([O:11][C:12]4[CH:17]=[CH:16][N:15]=[C:14]5[CH:18]=[C:19]([C:21]6[N:22]([CH3:26])[CH:23]=[CH:24][N:25]=6)[S:20][C:13]=45)=[CH:7][C:5]=3[S:6][C:2]=2[CH3:1])=[O:29])[CH2:36][CH2:35]1
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Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 221435462-Methyl-6-{[2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy}benzo[b]thiophene-3-carboxylic acid

Produkt 1

HCID 207679062-Methyl-6-{[2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy}benzo[b]thiophene-3-carboxylic acid cyclopropylamide
Ausbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-methyl-6-{[2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yl]oxy}benzo[b]thiophene-3-carboxylic acid 117b (75 mg, 0.18 mmole) in DMF (1.5 mL) at 0° C. were added N,N-diisopropylethylamine (68 μL, 0.39 mmole) and HBTU (100 mg, 0.27 mmole). The reaction mixture was stirred 30 min at 0° C. then warmed to room temperature and stirred 18 hr. The mixture was poured onto H2O (25 mL) and the precipitate was collected by vacuum filtration. The filter paper was extracted with a mixture of CH2Cl2 (10 mL) and MeOH (10 mL). The solution was concentrated and the crude mixture was purified by silica gel chromatography (5% MeOH/EtOAc) to afford a pale yellow solid (58 mg, 71%). 1H NMR (DMSO-d6, 300 MHz) δ8.52 (1H, d, J=5.46 Hz), 8.46 (1H, d, J=4.33 Hz), 7.95 (1H, d, J=2.26 Hz), 7.88 (1H, s), 7.80 (1H, d, J=8.67 Hz), 7.40 (1H, s), 7.32 (1H, dd, J=2.26, 8.85 Hz), 7.02 (1H, s), 6.70 (1H, d, J=5.46 Hz), 3.98 (3H, s), 2.90 (1H, m), 2.57 (3H, s); 0.73 (2H, m), 0.57 (2H, m).

Aufarbeitung

  1. temperaturethen warmed to room temperature
  2. stirringstirred 18 hr
  3. additionThe mixture was poured onto H2O (25 mL)
  4. filtrationthe precipitate was collected by vacuum filtration
  5. extractionThe filter paper was extracted with a mixture of CH2Cl2 (10 mL) and MeOH (10 mL)
  6. concentrationThe solution was concentrated
  7. customthe crude mixture was purified by silica gel chromatography (5% MeOH/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-c2df7701505c4870ab09b6e367f795fc
Quelldatensatz
uspto-grants-2005_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06869962B2

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