Pyrrole → 1-Methyl-4-[1-methyl-4-[2-[4-(trifluoromethyl)phenylsulfonyl]ethoxycarbonylamino]-2-imidazolylcarbonylamino]-1H-pyrrole-2-carboxylic acid methyl ester

HRID 1883476ノート

反応式

HRID 1883476 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:13])[CH:7]=[C:8]([N+:10]([O-])=O)[CH:9]=1)=[O:4].N1C=CC=C1.[CH3:19][N:20]1[CH:24]=[C:23]([NH:25][C:26]([O:28][CH2:29][CH2:30][S:31]([C:34]2[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=2)(=[O:33])=[O:32])=[O:27])[N:22]=[C:21]1[C:44](O)=[O:45].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.C(Cl)Cl.[Pd]>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:13])[CH:7]=[C:8]([NH:10][C:44]([C:21]2[N:20]([CH3:19])[CH:24]=[C:23]([NH:25][C:26]([O:28][CH2:29][CH2:30][S:31]([C:34]3[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:41])[F:42])=[CH:36][CH:35]=3)(=[O:32])=[O:33])=[O:27])[N:22]=2)=[O:45])[CH:9]=1)=[O:4]

参加物

10

反応物 6

HCID 8027PyrroleHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2759930Methyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylateHCID 2774761Tetramethylfluoroformamidinium hexafluorophosphateHCID 235107761-Methyl-4-[2-[4-(trifluoromethyl)phenylsulfonyl]ethoxycarbonylamino]-1H-imidazole-2-carboxylic acid

生成物 1

HCID 207406571-Methyl-4-[1-methyl-4-[2-[4-(trifluoromethyl)phenylsulfonyl]ethoxycarbonylamino]-2-imidazolylcarbonylamino]-1H-pyrrole-2-carboxylic acid methyl ester収率 63.01%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1-Methyl-4-nitropyrrole-2-carboxylic acid methyl ester (65.68 mg, 0.3567 mmol) was dissolved in EA (10 ml) and 10% Pd/C (10 mg) 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 a pyrrole-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) MF (6 ml) and DCM (2 ml) was added thereto, TFFH (83.37 mg, 0.3567 mmol), HOBt (64.73 mg, 0.4748 mmol) and DIEA (82.84 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-pyrrole-2-carboxylic acid methyl ester (41.7 mg, 63.01%) of a pale yellow solid.

後処理

  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

出典と根拠

ORDレコード
ord-797d5a9ffa454d65966a1241fd038044
出典データセット
uspto-grants-2004_07
特許番号
US06759511B2

反応ノート

読み込み中…