Pyridine → 1-phenyl-3-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-1H-pyrazole-4-carboxylic acid trimethylsilylethyl ester

HRID 413693Notes

Reaction equation

HRID 413693 reaction equation
[NH2:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])=[O:8])=[CH:5][N:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:3]=1.N1C=CC=CC=1.[C:28](Cl)(Cl)=[O:29].[C:32]1([C:38]2[CH:39]=[CH:40][C:41]3[O:45][C:44]([CH2:46][OH:47])=[CH:43][C:42]=3[CH:48]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:13][Si:12]([CH2:11][CH2:10][O:9][C:7]([C:6]1[C:2]([NH:1][C:28]([O:47][CH2:46][C:44]2[O:45][C:41]3[CH:40]=[CH:39][C:38]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)=[CH:48][C:42]=3[CH:43]=2)=[O:29])=[N:3][N:4]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:5]=1)=[O:8])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 113585882-(Trimethylsilyl)ethyl 3-amino-1-phenylpyrazol-4-carboxylateHCID 113790942-Hydroxymethyl-5-phenyl-benzofuran

Product 1

HCID 113303421-phenyl-3-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-1H-pyrazole-4-carboxylic acid trimethylsilylethyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent3×

Conditions

Temperature
90 °C

Procedure

To a solution of 2-(trimethylsilyl)ethyl 3-amino-1-phenylpyrazol-4-carboxylate (967 mg, 3.1 mmol) in 11 ml dry toluene and pyridine (504 mg, 0.52 mL, 6.3 mmol) was added a phosgene solution (2.4 mL of a 1.93M toluene solution, 4.62 mmol) under nitrogen. A white precipitate formed immediately, and the mixture was heated at 90° C. for 30 min. The reaction mixture was cooled to room temperature, and filtered. The filtrate was taken to dryness. (5-Phenyl-benzofuran-2-yl)-methanol 1 (556 mg, 2.48 mmol) and DMAP (40 mg, 0.33 mmol) in 15 mL toluene were added to the residue under nitrogen. The reaction mixture was heated at 75° C. for 4 h, then concentrated to dryness. Purification by chromatography afforded 1.28 g of 1-phenyl-3-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-1H-pyrazole-4-carboxylic acid trimethylsilylethyl ester, as a pale yellow solid.

Workup

  1. customA white precipitate formed immediately
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. temperatureThe reaction mixture was heated at 75° C. for 4 h
  5. concentrationconcentrated to dryness
  6. customPurification by chromatography

Sources & evidence

ORD record
ord-635364e1a78b4e689fd2248668485038
Source dataset
uspto-grants-2003_05
Patent number
US06569860B2

Reaction notes

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