HCID 178500481, Verbindung → HCID 178500482, Verbindung

HRID 982317Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 982317
[OH:1][C:2]1[N:7]([C:8]#[C:9][C:10]2[CH:29]=[CH:28][C:13]([C:14]([NH:16][C@H:17]([C:24]([O:26][CH3:27])=[O:25])[CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[O:15])=[CH:12][CH:11]=2)[CH:6]=[N:5][C:4]2=[N:30][CH:31]=[CH:32][C:3]=12>CO.C(Cl)Cl.[Pd]>[OH:1][C:2]1[N:7]([CH2:8][CH2:9][C:10]2[CH:29]=[CH:28][C:13]([C:14]([NH:16][C@H:17]([C:24]([O:26][CH3:27])=[O:25])[CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[O:15])=[CH:12][CH:11]=2)[CH:6]=[N:5][C:4]2=[N:30][CH:31]=[CH:32][C:3]=12

Komponenten

5

Edukt 1

HCID 178500481HCID 178500481, Verbindung

Produkt 1

HCID 178500482HCID 178500482, VerbindungAusbeute 60,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 1.1 g of dimethyl N-[4-(4-hydroxypyrrolo[2,3-d]pyrimidin-3-ylethynyl)benzoyl]-L-glutamate in 100 mL of 50% methanol in methylene chloride and 0.8 g of 3% palladium-on-carbon is hydrogenated at 50 p.s.i. for 24 hours, filtered, and concentrated under reduced pressure. Ether is added to the residue and the solid is collected by filtration and dried to yield 0.67 g of dimethyl N-{4-[2-(4-hydroxypyrrolo[2,3-d]pyrimidin-3-yl)ethyl]benzoyl}-L-glutamate. mp 170-172° C. 1NMR (d6 -DMSO) δ1.94-2.14 (m, 2H), 2.44 (t, J=7.4 Hz, 2H), 2.93-3.02 (m, 2H), 3.57 (s, 3H), 3.63 (s, 3H), 4.40-4.70 (m, 1H), 6.71 (s, 1H), 7.29 (d, J=8.2 Hz, 2 H), 7.77 (m, 3 H), 8.66 (d, J=7.4 Hz, 1H), 11.52 (s, 1H), 11.71 (s, 1H).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. additionEther is added to the residue
  4. filtrationthe solid is collected by filtration
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-413ae2af0e18455ea8d139703fb1d301
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04996206

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