Hydrochloric Acid → 2-[2-Amino-5-(4-methyl-piperazin-1-ylmethyl)-phenylamino]-4-phenyl-thiazole-5-carboxylic acid ethyl ester

HRID 1667680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667680
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12]2[CH:17]=[C:16]([CH2:18][N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)[CH:15]=[CH:14][C:13]=2[N+:26]([O-])=O)=[N:8][C:7]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:5])[CH3:2].Cl>[Zn].O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12]2[CH:17]=[C:16]([CH2:18][N:19]3[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]3)[CH:15]=[CH:14][C:13]=2[NH2:26])=[N:8][C:7]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:5])[CH3:2]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 866428062-[5-(4-Methyl-piperazin-1-ylmethyl)-2-nitro-phenylamino]-4-phenyl-thiazole-5-carboxylic acid ethyl ester

Produkt 1

HCID 866428072-[2-Amino-5-(4-methyl-piperazin-1-ylmethyl)-phenylamino]-4-phenyl-thiazole-5-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 0.066 g of 2-[5-(4-methyl-piperazin-1-ylmethyl)-2-nitro-phenylamino]-4-phenyl-thiazole-5-carboxylic acid ethyl ester (VI.1c), 0.5 mL of 1M hydrochloric acid, 2 mL of tetrahydrofuran was added 0.060 g of zinc powder. The suspension was stirred at ambient temperature for 2 hours. The solid was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was diluted with 2 mL of saturated sodium bicarbonate, 10 mL of water and extracted three times with 5 mL of dichloromethane. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 2-[2-amino-5-(4-methyl-piperazin-1-ylmethyl)-phenylamino]-4-phenyl-thiazole-5-carboxylic acid ethyl ester (VII.1a) as a yellow oil. This material was carried to next step of reaction without further purification.

Aufarbeitung

  1. customThe solid was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was diluted with 2 mL of saturated sodium bicarbonate, 10 mL of water
  4. extractionextracted three times with 5 mL of dichloromethane
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f1c4c6dd5e0847489ebd60f2cf852af5
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044213B2

Notizen zur Reaktion

Wird geladen…