Formaldehyde → (S)-7-Chloro-10-[3-(3-methoxy-propyl)-4-methyl-piperazin-1-yl]-4H-3-thia-4,9-diaza-benzo[f]azulene

HRID 131478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 131478
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]2[NH:6][C:7]3[S:8][CH:9]=[CH:10][C:11]=3[C:12]([N:14]3[CH2:19][CH2:18][NH:17][C@@H:16]([CH2:20][CH2:21][CH2:22][O:23][CH3:24])[CH2:15]3)=[N:13][C:4]=2[CH:3]=1.C=O.[C:29](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]2[NH:6][C:7]3[S:8][CH:9]=[CH:10][C:11]=3[C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH3:29])[C@@H:16]([CH2:20][CH2:21][CH2:22][O:23][CH3:24])[CH2:15]3)=[N:13][C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 136090412(S)-7-Chloro-10-[3-(3-methoxy-propyl)-piperazin-1-yl]-4H-3-thia-4,9-diaza-benzo[f]azulene

Produkt 1

HCID 136090372(S)-7-Chloro-10-[3-(3-methoxy-propyl)-4-methyl-piperazin-1-yl]-4H-3-thia-4,9-diaza-benzo[f]azuleneAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Combine (S)-7-chloro-10-[3-(3-methoxy-propyl)-piperazin-1-yl]-4H-3-thia-4,9-diaza-benzo[f]azulene (280.3 mg, 0.72 mmol), formaldehyde (64.0 μL, 0.79 mmol, 37% in water), and dichloromethane (10.0 ml). Stir the mixture at ambient temperature for 5 minutes and then add sodium triacetoxyborohydride (227.9 mg, 1.08 mmol). After stirring for 30 minutes at ambient temperature, quench the reaction with saturated sodium bicarbonate. Remove the organic portion and wash (brine), dry (sodium sulfate), and reduce the extracts to residue. Purify the residue on silica gel using a gradient of dichloromethane to dichloromethane/methanol (90:10) to give 223.0 mg (77%) of the title compound: mass spectrum (ion spray): m/z=405.1 (M+1).

Aufarbeitung

  1. stirringAfter stirring for 30 minutes at ambient temperature
  2. customquench
  3. customthe reaction with saturated sodium bicarbonate
  4. customRemove the organic portion
  5. washwash (brine)
  6. dry with materialdry (sodium sulfate)
  7. customPurify the residue on silica gel using a gradient of dichloromethane to dichloromethane/methanol (90:10)

Quellen und Nachweise

ORD-Eintrag
ord-1d801437e9944a0cb87383faac03d8e7
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384934B2

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