1,2-Dichloroethane → HCID 178462812, Verbindung

HRID 1884914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1884914
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[NH2:27][C:28]1[CH:29]=[C:30]([NH:34][C:35]2[N:43]=[C:42]([NH:44][CH:45]3[CH2:50][CH2:49][CH:48]([OH:51])[CH2:47][CH2:46]3)[N:41]=[C:40]3[C:36]=2[N:37]=[CH:38][N:39]3[CH2:52][CH3:53])[CH:31]=[CH:32][CH:33]=1>CN(C=O)C>[CH2:52]([N:39]1[CH:38]=[N:37][C:36]2[C:40]1=[N:41][C:42]([NH:44][C@H:45]1[CH2:50][CH2:49][C@H:48]([OH:51])[CH2:47][CH2:46]1)=[N:43][C:35]=2[NH:34][C:30]1[CH:29]=[C:28]([NH:27][C:10](=[O:12])[C:9]#[C:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH:33]=[CH:32][CH:31]=1)[CH3:53]

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 186072-(4-Chlorophenyl)-2-propynoic acidHCID 757711-HydroxybenzotriazoleHCID 23504692HCID 23504692, Verbindung

Produkt 1

HCID 178462812HCID 178462812, VerbindungAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To the solution of 190 mg (1 mmol) of (4-chlorophenyl)-propargylic acid in 20 ml of DMF at 0° C. is added 165 mg (1.1 mmol) of HOBT and 210 mg (1.1 mmol) of EDC. After 3 h at 0° C., 367 mg (1 mmol) of 4-[6-(3-Amino-phenylamino)-9-ethyl-9H-purin-2-ylamino]-cyclohexanol (example 77, stage 1.2) is added. After 1 h at 0° C. and 2.5 h at RT, the solvent was removed under reduced pressure. The crude product is purified by means of column chromatography on silica gel, trituration in diethyl ether and recrystallisation from ethanol to obtain 110 mg (0.21 mmol) of N-{3-[9-Ethyl-2-(trans-4-hydroxy-cyclohexylamino)-9H-purin-6yl-amino]-phenyl}-3-(4-chlorophenyl)-propargylic acid amide.

Aufarbeitung

  1. waitAfter 1 h at 0° C.
  2. custom2.5 h at RT, the solvent was removed under reduced pressure
  3. customThe crude product is purified by means of column chromatography on silica gel, trituration in diethyl ether
  4. customrecrystallisation from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-09a13aa4c3644918948888d8bc4e2169
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06767906B2

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