Sodium Bisulfite → 4-((2-(5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-1H-benzo[d]imidazol-6-yl)methyl)morpholine

HRID 1047553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047553
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)[N:8]=[C:7]2[CH:19]=O)([O-:3])=[O:2].[O:21]1[CH2:26][CH2:25][N:24]([CH2:27][C:28]2[CH:29]=[C:30]([NH2:35])[C:31]([NH2:34])=[CH:32][CH:33]=2)[CH2:23][CH2:22]1.S(=O)(O)[O-].[Na+]>C1COCC1.Cl.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)[N:8]=[C:7]2[C:19]1[NH:35][C:30]2[CH:29]=[C:28]([CH2:27][N:24]3[CH2:23][CH2:22][O:21][CH2:26][CH2:25]3)[CH:33]=[CH:32][C:31]=2[N:34]=1)([O-:3])=[O:2]

Komponenten

7

Edukt 3

HCID 23665763Sodium BisulfiteHCID 251933094-(Morpholinomethyl)benzene-1,2-diamineHCID 866732115-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carbaldehyde

Produkt 1

HCID 1363522584-((2-(5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-1H-benzo[d]imidazol-6-yl)methyl)morpholineAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-Nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3-carbaldehyde (85 mg, 0.309 mmol) and 4-(morpholinomethyl)benzene-1,2-diamine (64 mg, 0.309 mmol) were dissolved in dry THF (8 mL) and 2N HCl (1 drop) was added. The solution was heated at a gentle reflux for 30 min and then 1N sodium bisulfite (1 mL) was added. After overnight at reflux, the solution was cooled to room temperature, and diluted with ethyl acetate (40 mL). The mixture was washed with water and brine, dried over Na2SO4, and concentrated. Purification by flash chromatography (20% ethyl acetate/hexane) afforded the title compound as a pale yellow solid in a 50% yield. 1H NMR: (400 MHz, CD3OD): δ 9.42 (d, 1H, J=2.0 Hz), 8.32 (dd, 1H, J=2.0 and 8.8 Hz), 7.92-7.87 (m, 1H), 7.67 (m, 2H), 7.32 (d, 1H, J=8.4 Hz), 5.97 (dd, 1H, J=2.8 and 8.8 Hz), 3.99 (m, 1H), 3.88-3.82 (m, 1H), 3.72 (m, 6H), 2.57 (m, 5H), 2.19 (m, 2H), 1.88 (m, 1H), 1.73 (m, 2H).

Aufarbeitung

  1. temperatureThe solution was heated at
  2. temperaturea gentle reflux for 30 min
  3. temperatureAfter overnight at reflux
  4. washThe mixture was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by flash chromatography (20% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-74eefaf9dffc4426a84aafaa6e95e62c
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569511B2

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