Methanol → Methyl 3-({4-[(dimethylamino)carbonyl]phenyl}amino)-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate

HRID 2364257Notes

Reaction equation

HRID 2364257 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:13]([C:26]([OH:28])=[O:27])=[N:14][CH:15]=[C:16]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH:17]=2)=[CH:7][CH:6]=1)=[O:4].CO.[CH3:32][Si](C=[N+]=[N-])(C)C.CO.ClCCl>C(#N)C>[CH3:29][N:2]([CH3:1])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:13]([C:26]([O:28][CH3:32])=[O:27])=[N:14][CH:15]=[C:16]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH:17]=2)=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 21226129Dichloromethane methanolHCID 694827073-({4-[(Dimethylamino)carbonyl]phenyl} amino)-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylic acid

Product 1

HCID 69480335Methyl 3-({4-[(dimethylamino)carbonyl]phenyl}amino)-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylateYield 49.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-({4-[(dimethylamino)carbonyl]phenyl} amino)-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylic acid (79 mg, 0.201 mmol) was dissolved in a 9:1 acetonitrile:methanol solution (5 mL) and trimethylsilyldiazomethane (0.3 mL, 0.603 mmol) was added and the reaction was stirred at ambient temperature until complete by TLC (10% methanol/dichloromethane). The mixture was concentrated under reduced pressure, aqueous sodium bicarbonate was added, and the aqueous layer was extracted with chloroform. The combined organics were washed with brine and dried over sodium sulfate to yield methyl 3-({4-[(dimethylamino)carbonyl]phenyl}amino)-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (40.5 mg, 49% yield). 1H NMR (CDCl3) δ 9.49 (s, 1 H), 8.00 (s, 1 H), 7.34-7.36 (m, 3 H), 7.12-7.05 (m, 4 H), 6.97-6.94 (m, 2 H), 3.97 (s, 3 H), 3.87 (s, 2 H), 3.07 (br s, 3 H), 3.02 (br s, 3 H); MS m/z 408 (M+1).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure, aqueous sodium bicarbonate
  2. additionwas added
  3. extractionthe aqueous layer was extracted with chloroform
  4. washThe combined organics were washed with brine
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-8e1ca72e539f4f8d9f5b860cb0f509ee
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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