Nitrogen → 5-[4-(2-Chloro-benzyloxycarbonylamino)-pyrazol-1-ylmethyl]-furan-2-carboxylic acid methyl ester

HRID 2064912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2064912
N#N.[CH3:3][O:4][C:5]([C:7]1[O:8][C:9]([CH2:12][N:13]2[CH:17]=[C:16]([NH2:18])[CH:15]=[N:14]2)=[CH:10][CH:11]=1)=[O:6].CCN(C(C)C)C(C)C.[CH:28]1[CH:33]=[C:32]([CH2:34][O:35][C:36](Cl)=[O:37])[C:31]([Cl:39])=[CH:30][CH:29]=1>C(Cl)Cl>[CH3:3][O:4][C:5]([C:7]1[O:8][C:9]([CH2:12][N:13]2[CH:17]=[C:16]([NH:18][C:36]([O:35][CH2:34][C:32]3[CH:33]=[CH:28][CH:29]=[CH:30][C:31]=3[Cl:39])=[O:37])[CH:15]=[N:14]2)=[CH:10][CH:11]=1)=[O:6]

Komponenten

6

Edukt 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 40723422-Chlorobenzyl chloroformateHCID 669288905-(4-Amino-pyrazol-1-ylmethyl)-furan-2-carboxylic acid methyl ester

Produkt 1

HCID 33347405-[4-(2-Chloro-benzyloxycarbonylamino)-pyrazol-1-ylmethyl]-furan-2-carboxylic acid methyl 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 5-(4-amino-pyrazol-1-ylmethyl)-furan-2-carboxylic acid methyl ester (2.90 g, 13.10 mmol) in CH2Cl2 (58.0 mL) was treated with DIPEA (3.37 mL, 19.66 mmol) followed by 2-chlorobenzylchloroformate (2.69 mL, 17.04 mmol). The reaction mixture was stirred at rt for 4 h before being quenched with water (100 mL), extracted with CH2Cl2 (3×50 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (50:50 hept-EA) gave the title compound as a solid. TLC: rf (50:50 hept-EA)=0.22. LC-MS-conditions 02: tR=0.94 min; [M+H]+=390.37. 1H NMR (400 MHz, CDCl3) δ 3.89 (s, 3H), 5.29 (s, 2H), 5.31 (s, 2H), 6.39 (d, J=2.5 Hz, 1H), 6.75 (s, 1H), 7.12 (d, J=3.0 Hz, 1H), 7.23-7.31 (m, 2H), 7.38-7.42 (m, 1H), 7.43-7.46 (m, 2H), 7.75 (s, 1H).

Aufarbeitung

  1. custombefore being quenched with water (100 mL)
  2. extractionextracted with CH2Cl2 (3×50 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 (50:50 hept-EA)

Quellen und Nachweise

ORD-Eintrag
ord-2ee0235edafd4423bd3c976e7d9391d9
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288419B2

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