Formaldehyde → HCID 66919001, Verbindung

HRID 2354217Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2354217
[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH2:25][C@@H:26]5[CH2:30][CH2:29][CH2:28][NH:27]5)[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:3][CH2:2]1.[CH2:32]=O>C(O)=O>[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH2:25][C@@H:26]5[CH2:30][CH2:29][CH2:28][N:27]5[CH3:32])[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:2][CH2:3]1

Komponenten

4

Edukt 2

HCID 712FormaldehydeHCID 66918942HCID 66918942, Verbindung

Produkt 1

HCID 66919001HCID 66919001, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

N-Cyclopropyl-4-methyl-3-[4-oxo-6-[(2S)-pyrrolidin-2-ylmethoxy]quinazolin-3(4H)-yl]benzamide (0.15 g) and 38% aqueous formaldehyde (0.284 ml) were stirred in formic acid (3 ml) at 90° C. for 16 hours and then concentrated. The residue was partitioned between ethyl acetate and saturated aqueous NaHCO3 solution. The organic layer was washed with brine, dried (magnesium sulfate) and concentrated. Purification by column chromatography on a silica column eluting with 10% methanol/ethyl acetate followed by 10% methanol/ethyl acetate+1% aqueous ammonia solution to give the title compound (0.12 g) as a white foam solid; NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.70 (m, 2H), 1.70 (m, 3H), 1.99 (m, 1H), 2.14 (s, 3H), 2.22 (m, 1H), 2.39 (s, 3H), 2.62 (m, 1H), 2.85 (m, 1H), 2.96 (m, 1H), 3.99 (m, 1H), 4.09 (m, 1H), 7.52 (m, 2H), 7.60 (s, 1H), 7.73 (d, 1H), 7.83 (s, 1H), 7.91 (d, 1H), 8.19 (s, 1H), 8.42 (d, 1H); Mass Spectrum: M+H+ 433.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and saturated aqueous NaHCO3 solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated
  6. customPurification by column chromatography on a silica column
  7. washeluting with 10% methanol/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1ee75d9612234ce29d88d7aed7918117
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07750154B2

Notizen zur Reaktion

Wird geladen…