Acetic Acid → Carbonic acid 5-{(R)-(4-carbamimidoylphenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-m ethoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester 2-fluoro-1,1-dimethylethyl ester acetic acid salt

HRID 2089703

Reaktionsgleichung

Reaktionsgleichung von HRID 2089703
[F:1][CH2:2][C:3]([O:6][C:7](=[O:53])[O:8][CH2:9][O:10][C:11]1[N:12]([C:47]2[N:52]=[CH:51][CH:50]=[CH:49][N:48]=2)[N:13]=[C:14]([C@H:16]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([NH2:46])=[N:38]C(OCC(C)=C)=O)=[CH:33][CH:32]=2)[C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH2:26][CH2:27][OH:28])[C:18]=2[F:29])[N:15]=1)([CH3:5])[CH3:4].[C:54]([OH:57])(=[O:56])[CH3:55]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)C=O>[C:54]([OH:57])(=[O:56])[CH3:55].[F:1][CH2:2][C:3]([O:6][C:7](=[O:53])[O:8][CH2:9][O:10][C:11]1[N:12]([C:47]2[N:48]=[CH:49][CH:50]=[CH:51][N:52]=2)[N:13]=[C:14]([C@H:16]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([C:37](=[NH:38])[NH2:46])=[CH:33][CH:32]=2)[C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH2:26][CH2:27][OH:28])[C:18]=2[F:29])[N:15]=1)([CH3:5])[CH3:4]

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 86677424Carbonic acid 5-{(R)-(4-{amino[2-methylallyloxycarbonylimino]methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester 2-fluoro-1,1-dimethylethyl ester

Produkt 1

HCID 86677422Carbonic acid 5-{(R)-(4-carbamimidoylphenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-m ethoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester 2-fluoro-1,1-dimethylethyl ester acetic acid salt

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

Under nitrogen atmosphere, to a mixture of carbonic acid 5-{(R)-(4-{amino-[2-methylallyloxycarbonylimino]methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester 2-fluoro-1,1-dimethylethyl ester (Example 56b, 63.5 mg), acetic acid (49 μL) and N,N-dimethylformamide (0.70 ml), tetrakis(triphenylphosphine) palladium (0) (4.9 mg) was added, and the resulting mixture was stirred at 45° C. for 15 hours. After cooling the mixture to room temperature, the reaction solution containing the captioned compound was divided into 3 equal lots, and used for the following reactions.

Aufarbeitung

  1. additionwas added
  2. temperatureAfter cooling the mixture to room temperature
  3. additionthe reaction solution containing the captioned compound

Quellen und Nachweise

ORD-Eintrag
ord-82ccc7894e414b3eb62068cda3a22475
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436009B2

Verknüpfte Notizen

Wird geladen…