Dichloromethane → HCID 178491126, Verbindung

HRID 230379

Reaktionsgleichung

Reaktionsgleichung von HRID 230379
[NH2:1][C@@H:2]([C:13]1[NH:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1)[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH:24](=O)[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1.[BH4-].ClCCl>CO>[CH3:32][O:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][NH:1][C@@H:2]([C:13]2[NH:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:17]=2)[CH2:3][C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][CH:5]=2)=[CH:26][CH:27]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 28123BorohydrideHCID 312444-MethoxybenzaldehydeHCID 178511782HCID 178511782, Verbindung

Produkt 1

HCID 178491126HCID 178491126, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

2-{(1R)-1-Amino-2-[indol-3-yl]ethyl}-4-phenyl-1H-imidazole (36.3 mg, 0.12 mmol) and p-anisaldehyde (12 μl, 0.1 mmol) in 1 mL of methanol were shaken for about 2 hours at about 22° C. Borohydride resin (76 mg, 2.5 mmol/g, AMBERLITE® IRA-400) was then added and the slurry was stirred overnight before addition of dichloromethane (1 mL) and aldehyde Wang resin (31 mg, 3.22 mmol/g, Novabiochem). After about 8 hours of stirring, the slurry was then filtered and evaporated in vacuo to give a yellow solid (32.2 mg. 76%). 1H-NMR (CDCl3, 100 MHz) δ: 8.88 (br s, 1H); 7.73-6.68 (m, 15H); 4.62 (s, 1H); 4.33 (dd, J=4.7 and 8.5 Hz, 1H); 3.81 (s, 2H); 3.74 (s, 3H); 3.27 (ABX system, 2H)); 2.26 (s, 1H). LC/MS: m/z=423 (M+H).

Aufarbeitung

  1. filtrationthe slurry was then filtered
  2. customevaporated in vacuo
  3. customto give a yellow solid (32.2 mg. 76%)

Quellen und Nachweise

ORD-Eintrag
ord-a0bf16d297d94a14881b5c0062947220
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566734B2

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