Toluene → HCID 178492952, compound

HRID 1157962Notes

Reaction equation

HRID 1157962 reaction equation
C([N:4]1[C:8]([C:9]([OH:11])=[O:10])=[C:7]([N:12]2[C:16](=[O:17])[NH:15][C:14]([CH:18]([NH:30][C:31]3[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[C:33]([CH2:39][NH:40]C(OC(C)(C)C)=O)[CH:32]=3)[C:19]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[CH:21][C:20]=3[F:29])=[N:13]2)[N:6]=[CH:5]1)C=C.CN1C(=O)CC(=O)N(C)C1=O.FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:29][C:20]1[CH:21]=[C:22]([O:27][CH3:28])[C:23]([O:25][CH3:26])=[CH:24][C:19]=1[CH:18]([NH:30][C:31]1[CH:32]=[C:33]2[C:34](=[CH:35][CH:36]=1)[C:37](=[NH:38])[NH:40][CH2:39]2)[C:14]1[NH:15][C:16](=[O:17])[N:12]([C:7]2[N:6]=[CH:5][NH:4][C:8]=2[C:9]([OH:11])=[O:10])[N:13]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 69860Dimethylbarbituric acidHCID 135999727HCID 135999727, compound

Product 1

HCID 178492952HCID 178492952, compoundYield 12.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-allyl-5-(3-{[3-(t-butoxycarbonylaminomethyl)-4-cyanophenylamino]-(2-fluoro-4,5-dimethoxyphenyl)methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)-3H-imidazole-4-carboxylic acid (2.5 mg) in dichloromethane (2 mL) there were added tetrakis(triphenylphosphine)palladium(0)(0.5 mg) and 1,3-dimethylbarbituric acid (1.5 mg) under a nitrogen atmosphere, and the mixture was stirred overnight at room temperature. Trifluoroacetic acid (0.4 mL) was added, the mixture was stirred at room temperature for 30 minutes, and then toluene (10 mL) was added to the mixture and the solvent in the mixture was distilled off. The residue was purified by reverse-phase high performance liquid chromatography (acetonitrile/water mixed solvent, 0.1% acetic acid) to obtain the target compound (0.25 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. distillationthe solvent in the mixture was distilled off
  3. customThe residue was purified by reverse-phase high performance liquid chromatography (acetonitrile/water mixed solvent, 0.1% acetic acid)

Sources & evidence

ORD record
ord-31263773bb2f4d81afd54afaa7b5f8ef
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

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