Imidazole → 1-Methyl-4-[1-methyl-4-[2-[4-(trifluoromethyl)phenylsulfonyl]ethoxycarbonylamino]-2-imidazolylcarbonylamino]-1H-imidazole-2-carboxylic acid ethyl ester

HRID 1883477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1883477
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:14])[CH:8]=[C:9]([N+:11]([O-])=O)[N:10]=1)=[O:5])[CH3:2].N1C=CN=C1.[CH3:20][N:21]1[CH:25]=[C:24]([NH:26][C:27]([O:29][CH2:30][CH2:31][S:32]([C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=2)(=[O:34])=[O:33])=[O:28])[N:23]=[C:22]1[C:45](O)=[O:46].CN(C(F)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CC(=O)OCC.CN(C=O)C.C(Cl)Cl.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:14])[CH:8]=[C:9]([NH:11][C:45]([C:22]2[N:21]([CH3:20])[CH:25]=[C:24]([NH:26][C:27]([O:29][CH2:30][CH2:31][S:32]([C:35]3[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:42])[F:43])=[CH:37][CH:36]=3)(=[O:33])=[O:34])=[O:28])[N:23]=2)=[O:46])[N:10]=1)=[O:5])[CH3:2]

Komponenten

11

Edukt 6

HCID 795ImidazoleHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2758876Ethyl 1-methyl-4-nitroimidazole-2-carboxylateHCID 2774761Tetramethylfluoroformamidinium hexafluorophosphateHCID 235107761-Methyl-4-[2-[4-(trifluoromethyl)phenylsulfonyl]ethoxycarbonylamino]-1H-imidazole-2-carboxylic acid

Produkt 1

HCID 207406551-Methyl-4-[1-methyl-4-[2-[4-(trifluoromethyl)phenylsulfonyl]ethoxycarbonylamino]-2-imidazolylcarbonylamino]-1H-imidazole-2-carboxylic acid ethyl esterAusbeute 54,45 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-Methyl-4-nitroimidazole-2-carboxylic acid ethyl ester (71.05 mg, 0.3567 mmol) was dissolved in EA (10 ml) and 10% Pd/C (10 mg, catalytic weight) was added thereto. The reaction solution was stirred for 10 hours at room temperature under hydrogen atmosphere to reduce a nitro group (NO2) into an amino group (NH2), whereby an imidazole-type amino acid was obtained. 10% Pd/C was filtered out by celite 545 and the filtrate was washed with EA and methanol. 1-Methyl-4-[2-(4-trifluoromethyl-benzenesulfonyl)-ethoxycarbonylamino]-1H-imidazole-2-carboxylic acid (50.10 mg, 0.1187 mmol) dissolved in a solvent mixture of anhydrous DMF (6 ml) and DCM (2 ml) was added thereto, TFFH (94.21 mg, 0.3567 mmol), HOBt (64.74 mg, 0.4748 mmol) and DIEA (82.85 ml, 0.4748 mmol) were also added thereto, and the reaction solution was reacted according to the same procedure as Step (4-1) of Example 2 to give 1-methyl-4-({1-methyl-4-[2-(4-trifluoromethyl-benzenesulfonyl)-ethoxycarbonylamino]-1H-imidazole-2-carbonyl}-amino)-1H-imidazole-2-carboxylic acid ethyl ester (37.00 mg, 54.45%) of a pale yellow solid.

Aufarbeitung

  1. customwas obtained
  2. filtration10% Pd/C was filtered out by celite 545
  3. washthe filtrate was washed with EA and methanol
  4. additionwas added
  5. customthe reaction solution was reacted

Quellen und Nachweise

ORD-Eintrag
ord-9038307f896948b084915511a3fc0681
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06759511B2

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