Formamide → HCID 86592859, compound

HRID 351263Notes

Reaction equation

HRID 351263 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[N:19]=[C:18]([C:29]([O:31]CC)=O)[CH:17]=2)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].C([NH2:39])=O>>[NH2:39][C:29]([C:18]1[CH:17]=[C:16]([C:13]2[CH:12]=[CH:11][C:10]([CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:15][CH:14]=2)[N:20]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[N:19]=1)=[O:31]

Participants

4

Reactant 3

HCID 713FormamideHCID 10942334Sodium MethoxideHCID 21091029HCID 21091029, compound

Product 1

HCID 86592859HCID 86592859, compound

Conditions

Temperature
70 °C

Procedure

A mixture of ethyl 5-(4-{[(tert-butoxycarbonyl)amino]-methyl}phenyl)-1-(4-methoxyphenyl)-1H-pyrazole-3-carboxylate (500 mg) and sodium methoxide (239 mg) in formamide 5 ml was stirred at 70° C. for 2 hours. The mixture was cooled to ambient temperature and partitioned between AcOEt and brine. The organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo to give tert-butyl {4-[3-(aminocarbonyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]benzyl}carbamate (512 mg) as an oil.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. custompartitioned between AcOEt and brine
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b33a8d586a946529c298e1726ea716c
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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