Imidazole → HCID 20740656, compound

HRID 1883473Notes

Reaction equation

HRID 1883473 reaction equation
[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])[CH:23]=[C:22]1[C:45](O)=[O:46].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.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:34])=[O:33])=[O:28])[CH:23]=2)=[O:46])[N:10]=1)=[O:5])[CH3:2]

Participants

10

Reactant 5

HCID 795ImidazoleHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 2758876Ethyl 1-methyl-4-nitroimidazole-2-carboxylateHCID 11293057HCID 11293057, compound

Product 1

HCID 20740656HCID 20740656, compoundYield 75.12%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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-pyrrole-2-carboxylic acid (49.98 mg, 0.1189 mmol) dissolved in a solvent mixture of anhydrous DMF (6 ml) and DCM (2 ml) was added thereto, PyBroP (166.29 mg, 0.3567 mmol) and DIEA (62.13 ml, 0.3567 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-pyrrole-2-carbonyl}-amino)--1H-imidazole-2-carboxylic acid ethyl ester (51.05 mg, 75.12%) of a pale yellow solid.

Workup

  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

Sources & evidence

ORD record
ord-ab3223bd7ee14960b4698503ac94f586
Source dataset
uspto-grants-2004_07
Patent number
US06759511B2

Reaction notes

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