Nitrogen → 4-[4-(2-Chloro-benzyloxycarbonylamino)-pyrazol-1-ylmethyl]-thiazole-2-carboxylic acid ethyl ester

HRID 2065022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2065022
N#N.[CH2:3]([O:5][C:6]([C:8]1[S:9][CH:10]=[C:11]([CH2:13][N:14]2[CH:18]=[C:17]([NH2:19])[CH:16]=[N:15]2)[N:12]=1)=[O:7])[CH3:4].CCN(C(C)C)C(C)C.[CH:29]1[CH:34]=[C:33]([CH2:35][O:36][C:37](Cl)=[O:38])[C:32]([Cl:40])=[CH:31][CH:30]=1>C(Cl)Cl>[CH2:3]([O:5][C:6]([C:8]1[S:9][CH:10]=[C:11]([CH2:13][N:14]2[CH:18]=[C:17]([NH:19][C:37]([O:36][CH2:35][C:33]3[CH:34]=[CH:29][CH:30]=[CH:31][C:32]=3[Cl:40])=[O:38])[CH:16]=[N:15]2)[N:12]=1)=[O:7])[CH3:4]

Komponenten

6

Edukt 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 40723422-Chlorobenzyl chloroformateHCID 669285564-(4-Amino-pyrazol-1-ylmethyl)-thiazole-2-carboxylic acid ethyl ester

Produkt 1

HCID 669288894-[4-(2-Chloro-benzyloxycarbonylamino)-pyrazol-1-ylmethyl]-thiazole-2-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 4-(4-amino-pyrazol-1-ylmethyl)-thiazole-2-carboxylic acid ethyl ester (1.43 g, 5.65 mmol) in CH2Cl2 (56.0 mL) was treated with DIPEA (1.15 mL, 8.47 mmol) followed by 2-chlorobenzylchloroformate (1.04 mL, 6.78 mmol). The reaction mixture was stirred at rt for 1 h before being quenched with water (50 mL), extracted with CH2Cl2 (3×40 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (96:4 CH2Cl2-MeOH) gave the title compound as a pink foam. TLC: rf (96:4 CH2Cl2-MeOH)=0.28. LC-MS-conditions 02: tR=0.99 min; [M+H]+=421.14.

Aufarbeitung

  1. custombefore being quenched with water (50 mL)
  2. extractionextracted with CH2Cl2 (3×40 mL)
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the residue by FC (96:4 CH2Cl2-MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-9066651e68a945f1a5ac0be5658afc38
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288419B2

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