Trimethylsilyl isocyanate → 4-{3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-3,6-dihydro-2H-pyridine-1-carboxamide

HRID 2046923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2046923
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[CH2:22][CH2:23][NH:24][CH2:25][CH:26]=3)[CH:19]=2)[NH:14][CH:13]=1)[CH3:11].C[Si]([N:31]=[C:32]=[O:33])(C)C.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[CH2:22][CH2:23][N:24]([C:32]([NH2:31])=[O:33])[CH2:25][CH:26]=3)[CH:19]=2)[NH:14][CH:13]=1)[CH3:11]

Komponenten

5

Edukt 3

HCID 70696Trimethylsilyl isocyanateHCID 81531DiisopropylethylamineHCID 673640813-[1-(2,6-Dichloro-3-fluorophenyl)-ethyl]-5-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 674021664-{3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-3,6-dihydro-2H-pyridine-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3-[1-(2,6-dichloro-3-fluorophenyl)-ethyl]-5-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine (12.0 mg, 0.0307 mmol), trimethylsilyl isocyanate (8.32 μL, 0.0615 mmol), DIPEA (26.8 μL, 0.154 mmol) and DMF (0.5 mL) was stirred at rt for 20 min. The solution was concentrated in vacuo, redissolved in MeOH (0.5 mL) and purified via HPLC. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ=1.87 (d, J=7.1 Hz, 3 H), 2.28-2.51 (m, 2 H), 3.60 (t, J=5.8 Hz, 2 H), 4.02 (q, J=2.5 Hz, 2 H), 5.26 (q, J=7.1 Hz, 1 H), 5.88-5.94 (m, 1 H), 7.18 (t, J=8.6 Hz, 1 H), 7.29 (d, J=2.0 Hz, 1 H), 7.32-7.55 (m, 2 H), 8.23 (br. s., 1 H). MS (ES+): m/z 433.02 (100) [MH+]. HPLC: tR=3.15 min (ZQ3, polar—5 min).

Aufarbeitung

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionredissolved in MeOH (0.5 mL)
  3. custompurified via HPLC
  4. additionThe fractions containing the pure product
  5. concentrationwere concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-988fe362d6c94d88ac9d8688a56c68b7
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592448B2

Notizen zur Reaktion

Wird geladen…