Trifluoroacetic acid → 3-(1,2,3,4-Tetrahydro-6-isoquinolinyl)benzamide

HRID 471855Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471855
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)[CH:7]=[CH:8][CH:9]=1)=[O:3].[SiH](CC)(CC)CC.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:16]1[C:17]2[C:12](=[CH:11][C:10]([C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:2]([NH2:1])=[O:3])=[CH:19][CH:18]=2)[CH2:13][CH2:14][NH:15]1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 582763421,1-dimethylethyl 6-[3-(aminocarbonyl)phenyl]-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Produkt 1

HCID 582764713-(1,2,3,4-Tetrahydro-6-isoquinolinyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1,1-dimethylethyl 6-[3-(aminocarbonyl)phenyl]-3,4-dihydro-2(1H)-isoquinolinecarboxylate (0.725 g; 2.20 mmol; I-VII-9) and Et3SiH (0.88 mL; 5.5 mmol) in CH2Cl2 (25 mL) at room temperature was added TFA (10 mL) in one portion. The mixture was aged 3 h and concentrated in vacuo (2×PhMe chase). The residue was partitioned between satd Na2CO3/CHCl3 (Note 1), layers were separated and the aqueous layer was extracted with CHCl3 (×4). Combined organics were washed (water, brine), dried over Na2SO4 and concentrated in vacuo, affording the title compound as a colorless solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.76 (t, J=5.7 Hz, 2H), 2.96 (t, J=5.8 Hz, 2H), 3.87 (s, 2H), 7.11 (d, J=7.9 Hz, 1H), 7.40-7.48 (m, 3H), 7.51 (t, J=7.8 Hz, 1H), 7.78 (ddd, J=7.7, 1.8, 1.1 Hz, 1H), 7.82 (ddd, J=7.8, 1.4, 1.3 Hz, 1H), 8.10 (s, 1H), 8.12 (t, J=1.6 Hz, 1H).

Aufarbeitung

  1. concentrationconcentrated in vacuo (2×PhMe chase)
  2. customThe residue was partitioned between satd Na2CO3/CHCl3 (Note 1), layers
  3. customwere separated
  4. extractionthe aqueous layer was extracted with CHCl3 (×4)
  5. washCombined organics were washed (water, brine)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2a20096f5135446593016742ab7526a4
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633175B2

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