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

HRID 1883476노트

반응식

HRID 1883476 반응식
[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]

참가 물질

10

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-797d5a9ffa454d65966a1241fd038044
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06759511B2

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