Ammonium formate → HCID 59469086, Verbindung

HRID 1809019Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1809019
[Cl:1][C:2]1[C:3]2[N:4]([CH:29]=[CH:30][N:31]=2)[CH:5]=[C:6]([C:17]([N:19]2[CH2:22][C:21]([CH:24]([N+:26]([O-])=O)[CH3:25])([OH:23])[CH2:20]2)=[O:18])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=1[F:16].C([O-])=O.[NH4+]>O1CCCC1.O.[Fe]>[NH2:26][CH:24]([C:21]1([OH:23])[CH2:22][N:19]([C:17]([C:6]2[C:7]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=3[F:16])=[C:2]([Cl:1])[C:3]3[N:4]([CH:29]=[CH:30][N:31]=3)[CH:5]=2)=[O:18])[CH2:20]1)[CH3:25]

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 67051709HCID 67051709, Verbindung

Produkt 1

HCID 59469086HCID 59469086, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 21881883Oxolane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 1-({8-chloro-7-[(2-fluoro-4-iodophenyl)amino]imidazo[1,2-a]pyridin-6-yl}carbonyl)-3-(1-nitroethyl)azetidin-3-ol (195 mg 0.35 mmol) in tetrahydrofuran/water (5 mL, 4:1) was added iron powder (193 mg, 3.5 mmol) and ammonium formate (438 mg, 7.0 mmol). The mixture was stirred at 80° C. for 1 hour, then cooled to room temperature and filtered through a pad of celite. The celite was washed three times with boiling ethanol (20 mL). The filtrate was concentrated in vacuo and the residue was diluted with ethyl acetate. The precipitate which formed was filtered through a pad a celite and the filtrate was partitioned with water. The aqueous portion was extracted twice with ethyl acetate. The combined organic portion was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford a yellow residue which was purified by preparative reverse phase HPLC. The isolated product was concentrated in vacuo to afford mg, 0.05 mmol (15%) of 3-(1-aminoethyl)-1-({8-chloro-7-[(2-fluoro-4-iodophenyl)amino]imidazo[1,2-a]pyridin-6-yl}carbonyl)azetidin-3-ol acetate salt as a white solid. 1H NMR (400 MHz, DMSO): 8.79 (s, 1H), 8.00 (s, 1H), 7.61 (s, 1H), 7.54 (d, 1H), 7.32 (d, 1H), 6.54-6.48 (m, 1H), 4.24-4.13 (m, 1H), 3.98-3.84 (m, 2H), 3.61-3.56 (m, 1H), 2.83 (q, 1H), 0.92-0.88 (m, 3H); MS (EI) for C19H18ClFIN5O2: 530 (MH+).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a pad of celite
  3. washThe celite was washed three times with boiling ethanol (20 mL)
  4. concentrationThe filtrate was concentrated in vacuo
  5. additionthe residue was diluted with ethyl acetate
  6. customThe precipitate which formed
  7. filtrationwas filtered through a pad a celite
  8. customthe filtrate was partitioned with water
  9. extractionThe aqueous portion was extracted twice with ethyl acetate
  10. washThe combined organic portion was washed with brine
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customto afford a yellow residue which
  15. customwas purified by preparative reverse phase HPLC
  16. concentrationThe isolated product was concentrated in vacuo
  17. customto afford mg

Quellen und Nachweise

ORD-Eintrag
ord-6fc8b893744c46a08ee0493bf2ba7d1c
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362002B2

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