Sodium Iodide → HCID 58379684, Verbindung

HRID 1038991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1038991
Cl[CH2:2][C:3]([CH3:38])([CH3:37])[C:4]([N:6]([C@H:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29]1)[CH2:7]/[CH:8]=[CH:9]/[C:10]1[CH:11]=[C:12]2[CH2:27][C@@:17]3([C:25]4[C:20](=[N:21][CH:22]=[CH:23][CH:24]=4)[NH:19][C:18]3=[O:26])[CH2:16][C:13]2=[N:14][CH:15]=1)=[O:5].[Na+].[I-:40]>CC(C)=O>[C@H:28]1([N:6]([CH2:7]/[CH:8]=[CH:9]/[C:10]2[CH:11]=[C:12]3[CH2:27][C@@:17]4([C:25]5[C:20](=[N:21][CH:22]=[CH:23][CH:24]=5)[NH:19][C:18]4=[O:26])[CH2:16][C:13]3=[N:14][CH:15]=2)[C:4](=[O:5])[C:3]([CH3:37])([CH3:38])[CH2:2][I:40])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29]1

Komponenten

4

Edukt 2

HCID 5238Sodium IodideHCID 58379679HCID 58379679, Verbindung

Produkt 1

HCID 58379684HCID 58379684, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 3-chloro-N-[(1R)-2,3-dihydro-1H-inden-1-yl]-2,2-dimethyl-N-{(2E)-3-[(6S)-2′-oxo-1′,2′,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridin]-3-yl]prop-2-en-1-yl}propanamide (120. mg, 0.228 mmol) in acetone (2.3 mL) was added NaI (683 mg, 4.55 mmol). This mixture was heated to 120° C. in a microwave reactor for 30 minutes. After cooling, the bulk of the acetone was removed in vacuo and the residue was partitioned between DCM and water. The organics were dried over sodium sulfate, filtered, and concentrated in vacuo to provide a residue. The residue was then applied to a silica gel column for purification, eluting with a gradient of 1-8% MeOH (containing 10% conc. NH4OH) in DCM to provide the title compound. MS: m/z=619 (M+1).

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe bulk of the acetone was removed in vacuo
  3. customthe residue was partitioned between DCM and water
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide a residue
  8. customThe residue was then applied to a silica gel column for purification
  9. washeluting with a gradient of 1-8% MeOH (containing 10% conc. NH4OH) in DCM

Quellen und Nachweise

ORD-Eintrag
ord-8e2a6a266ad24062aec5eb4560ddcb24
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552023B2

Notizen zur Reaktion

Wird geladen…