Nitrogen → 6-{4-[1-(4,5-dihydro-oxazol-2-yl)-cyclopropyl]-phenyl}-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester

HRID 971153Notes

Reaction equation

HRID 971153 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[CH2:13][CH2:12][NH:11][C:10](=[O:15])[C:9]=2[N:8]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:7]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].N1[C:43]2[C:34](=[CH:35][CH:36]=[C:37]3[C:42]=2N=[CH:40][CH:39]=[CH:38]3)C=CC=1.[N:44]#N.[CH3:46][CH2:47][O:48][C:49](C)=O>CS(C)=O.[Cu](I)I>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[CH2:13][CH2:12][N:11]([C:34]3[CH:35]=[CH:36][C:37]([C:38]4([C:49]5[O:48][CH2:47][CH2:46][N:44]=5)[CH2:39][CH2:40]4)=[CH:42][CH:43]=3)[C:10](=[O:15])[C:9]=2[N:8]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

8

Reactant 5

HCID 947NitrogenHCID 13181,10-PhenanthrolineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 22240468Ethyl 1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo(3,4-c)pyridine-3-carboxylate

Product 1

HCID 695159716-{4-[1-(4,5-dihydro-oxazol-2-yl)-cyclopropyl]-phenyl}-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Part A. The product of Part A from Example 141 (0.10 g, 0.32 mmol) and 1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (0.10 g, 0.32 mmol) were dissolved in DMSO (1.5 mL). Potassium carbonate (1.3 g, 0.94 mmol), copper iodide (0.02 g, 0.10 mmol), and 1,10-phenanthroline (0.02 g, 0.11 mmol) were then added and the reaction was heated to 120° C. for 12 h under an environment of N2. The reaction was cooled, diluted with EtOAc, washed with H2O (2×), brine, dried over Na2SO4, filtered, and concentrated to dryness to give 6-{4-[1-(4,5-dihydro-oxazol-2-yl)-cyclopropyl]-phenyl}-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester. LC/MS (ESI+) 501.8 (M+H)+, tR=2.64 min (10–90% CH3CN/H2O in a 4-min run).

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with H2O (2×), brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-96694278d7104d879c0a8d979cd82b17
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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