Triethylamine → Genz-10850

HRID 842029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 842029
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl.Cl.[CH:15]1[C:27]2[CH:26]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C>ClCCl.CN(C1C=CN=CC=1)C>[CH:24]1[C:25]2[CH:26]([N:28]3[CH2:33][CH2:32][N:31]([C:10]([C:6]4[CH:5]=[C:4]5[C:9](=[CH:8][CH:7]=4)[NH:1][CH:2]=[CH:3]5)=[O:12])[CH2:30][CH2:29]3)[C:27]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]=2[CH:21]=[CH:22][CH:23]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 742801H-Indole-5-Carboxylic AcidHCID 27461801-(9H-fluoren-9-yl)piperazine Dihydrochloride

Produkt 1

HCID 447767Genz-10850

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Indole-5-carboxylic acid (17 mg, 0.11 mmole) and N-9-fluorenyl-piperazine dihydrochloride (32 mg, 0.1 mmole) were dissolved in 5 ml dichloromethane. To this solution was added triethylamine (2 eq. to neutralize HCl salt), catalytic DMAP and EDCI (33 mg, 0.11 mmole). The resulting mixture was stirred at room temperature overnight and was then worked up by washing sequentially with 1N HCl, saturated sodium bicarbonate, and saturated sodium chloride. The product was then purified by flash chromatography on silica gel (40:1 CHCl3/MeOH). 1H NMR (300 Mhz, CDCl3) δ 8.38 (s, 1H), 7.72-7.60 (m, 5H), 7.40-7.18 (m, 7H), 6.55 (d, 1H), 4.88 (s,1H), 3.60 (bs, 4H), 2.62 (bs, 4H).

Aufarbeitung

  1. washby washing sequentially with 1N HCl, saturated sodium bicarbonate, and saturated sodium chloride
  2. customThe product was then purified by flash chromatography on silica gel (40:1 CHCl3/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-ea8e4213f63649519ad707977dad32ba
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06372752B1

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