Benzaldehyde → HCID 21922957, Verbindung

HRID 1244904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1244904
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[N:13]=[C:12]([Cl:14])[N:11]=[C:10]2[C:6]=1[N:7]=[CH:8][N:9]2[CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.CO.[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([BH3-])#N.[Na+]>CCCCCC.CCOC(C)=O.C(O)(=O)C>[Cl:14][C:12]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:5]([NH:4][CH2:3][CH2:2][NH:1][CH:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:13]=1

Komponenten

8

Edukt 4

HCID 240BenzaldehydeHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 21922924N-(2-aminoethyl)-2-chloro-9-cyclopentyl-9H-purin-6-amine

Produkt 1

HCID 21922957HCID 21922957, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The operation is carried out as in Stage 2 of Example 7 starting from 141 mg of the product obtained in Stage 1 of Example 7, 2 ml of methanol, 0.7 ml (15 eq) of benzaldehyde and 0.1 ml of acetic acid then the reaction medium is agitated at ambient temperature for approximately 3 hours. Then 55 mg of sodium cyanoborohydride (NaBH3CN) is added and the reaction medium is agitated at ambient temperature for 1 hour. 10 ml AcOEt is added, followed by washing with 2×5 ml H2O, then 5 ml of a saturated aqueous solution of NaCl, drying and evaporating the solvent. After purification by chromatography on silica eluting with methylene chloride/ethyl acetate in a proportion of 70/30, the product obtained is impasted in hexane and in this way 143 mg of expected product is obtained.

Aufarbeitung

  1. stirringthe reaction medium is agitated at ambient temperature for 1 hour
  2. washby washing with 2×5 ml H2O
  3. dry with material5 ml of a saturated aqueous solution of NaCl, drying
  4. customevaporating the solvent
  5. customAfter purification by chromatography on silica eluting with methylene chloride/ethyl acetate in a proportion of 70/30
  6. customthe product obtained

Quellen und Nachweise

ORD-Eintrag
ord-8bdafb7bae3d43e993fae6d914101070
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07122669B1

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