5-Amino-2-chloropyridine → N-(6-Chloro-pyridin-3-yl)-2-(7-fluoro-1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetamide

HRID 29795

Reaktionsgleichung

Reaktionsgleichung von HRID 29795
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]1[C:11](=[O:20])[NH:12][CH2:13][CH:14]=[C:15]([CH2:16][C:17]([OH:19])=O)[C:5]2=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:54][C:55]1[N:60]=[CH:59][C:58]([NH2:61])=[CH:57][CH:56]=1>CN(C=O)C>[Cl:54][C:55]1[N:60]=[CH:59][C:58]([NH:61][C:17](=[O:19])[CH2:16][C:15]2[C:5]3[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=4)[NH:7][C:6]=3[C:11](=[O:20])[NH:12][CH2:13][CH:14]=2)=[CH:57][CH:56]=1

Komponenten

6

Edukt 4

HCID 793055-Amino-2-chloropyridineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59789203(7-Fluoro-1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetic acid

Produkt 1

HCID 59789199N-(6-Chloro-pyridin-3-yl)-2-(7-fluoro-1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (7-fluoro-1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetic acid, prepared as in reference 16, (25 mg, 0.091 mmol) in DMF (1 mL) is added DIEA (35.4 mg, 0.274 mmol), HATU (38.2 mg, 0.100 mmol) and 6-chloro-pyridin-3-ylamine (35.2 mg, 0.274 mmol). The mixture is stirred at room temperature for 2 hours and concentrated. The residue is purified by HPLC (C18 column, eluted with CH3CN/H2O with 0.05% TFA) to give N-(6-Chloro-pyridin-3-yl)-2-(7-fluoro-1-oxo-1,2,3,10-tetrahydro-azepino[3,4-b]indol-5-yl)-acetamide; 1H NMR (DMSO-d6) δ 3.43 (t, 2H, J=5.6 Hz), 3.84 (s, 2H), 5.96 (t, 1H, J=7.2 Hz), 7.12 (dt, 1H, J1=2.4 Hz, J2=8.8 Hz), 7.43 (d, 1H, J=8.8 Hz), 7.46 (dd, 1H, J1=4.4 Hz, J2=8.8 Hz), 7.67 (dd, 1H, J1=2.4 Hz, J2=10.8 Hz), 8.01 (dd, 1H, J1=2.8 Hz, J2=8.0 Hz), 8.19 (t, 1H, J=5.2 Hz), 8.54 (d, 1H, J=3.2 Hz), 10.48 (s, 1H), 12.04 (s, 1H); m/z [M++1] 385.0.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue is purified by HPLC (C18 column, eluted with CH3CN/H2O with 0.05% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-e16a5635d4fd4c6ca6988a6e0ec69f1f
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423031B2

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