Ethyl 4-butyrylbenzoate → Ethyl 4-(1-((6-(4-cyclopropyl-1H-pyrazol-1-yl)pyridin-3-yl)amino)butyl)benzoate

HRID 1520962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1520962
[C:1]([C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1)(=O)[CH2:2][CH2:3][CH3:4].[CH:17]1([C:20]2[CH:21]=[N:22][N:23]([C:25]3[N:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=3)[CH:24]=2)[CH2:19][CH2:18]1.[B][B][B][B][B][B][B][B][B][B]>CO>[CH:17]1([C:20]2[CH:21]=[N:22][N:23]([C:25]3[N:30]=[CH:29][C:28]([NH:31][CH:1]([C:6]4[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=4)[CH2:2][CH2:3][CH3:4])=[CH:27][CH:26]=3)[CH:24]=2)[CH2:19][CH2:18]1

Komponenten

5

Edukt 3

HCID 67980577Ethyl 4-butyrylbenzoateHCID 681567276-(4-cyclopropyl-1H-pyrazol-1-yl)pyridin-3-amineHCID 178419135HCID 178419135, Verbindung

Produkt 1

HCID 86669097Ethyl 4-(1-((6-(4-cyclopropyl-1H-pyrazol-1-yl)pyridin-3-yl)amino)butyl)benzoateAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-butyrylbenzoate (121 mg, 0.549 mmol) and 6-(4-cyclopropyl-1H-pyrazol-1-yl)pyridin-3-amine (0.110 g, 0.549 mmol) in methanol (1.3 ml) was added decaborane (27 mg, 0.22 mmol). The reaction was stirred for 12 hours at ambient temperature. The reaction mixture was quenched with aqueous 1.0M hydrochloric acid and concentrated in vacuo. The crude material was purified via ISCO MPLC (SiO2, 0-100% ethyl acetate in heptane) to yield the product (26 mg, 12%) as an oil. 1H NMR (400 MHz, CDCl3): δ 8.05 (s, 1H), 8.01 (d, J=8.2 Hz, 2H), 7.67 (br. s., 1H), 7.62 (d, J=9.0 Hz, 1H), 7.44 (s, 1H), 7.40 (d, J=8.2 Hz, 2H), 6.90 (d, J=6.8 Hz, 1H), 4.37 (q, J=7.2 Hz, 3H), 1.76-1.90 (m, 2H), 1.72 (tt, J=8.4, 5.1 Hz, 1H), 1.41-1.52 (m, 2H), 1.38 (t, J=7.1 Hz, 3H), 0.96 (t, J=7.3 Hz, 3H), 0.86 (ddd, J=8.2, 5.9, 3.9 Hz, 2H), 0.56 (dt, J=5.9, 4.1 Hz, 2H).

Aufarbeitung

  1. customThe reaction mixture was quenched with aqueous 1.0M hydrochloric acid
  2. concentrationconcentrated in vacuo
  3. customThe crude material was purified via ISCO MPLC (SiO2, 0-100% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-003062f379b140928718067808e5757c
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073871B2

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