Picolinic acid → HCID 21256696, compound

HRID 636289Notes

Reaction equation

HRID 636289 reaction equation
Cl.Cl.[C:3]1([NH2:10])[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.CCN(C(C)C)C(C)C.[CH:20]1[CH:21]=[CH:22][C:23]2N(O)N=[N:26][C:24]=2[CH:25]=1.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:36](O)=[O:37].CN([P+]([O:49]N1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[Na+].[Cl-]>CN(C=O)C.O.CCOC(C)=O>[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:36]([NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([NH:10][C:25](=[O:49])[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][N:26]=2)[CH:4]=1)=[O:37]

Participants

10

Reactant 6

HCID 1018Picolinic acidHCID 5234Sodium ChlorideHCID 109411,3-Benzenediamine dihydrochlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 21256696HCID 21256696, compoundYield 78.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1,3-phenylenediamine dihydrochloride (183 mg, 1.00 mmol) in DMF (10 mL) was added iPr2NEt (2.10 mL, 12.1 mmol), HOBt (407 mg, 3.00 mmol), picolinic acid (370 mg, 3.00 mmol), and BOP reagent (1.34 g, 3.00 mmol) in sequential fashion. After 18 h at room temperature, the reaction mixture was added to a rapidly-stirred mixture of EtOAc (50 mL), H2O (50 mL), and sat'd NaCl (50 mL). After stirring for ca 1 h, the phases were separated and the aqueous layer was extracted with EtOAc (50 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to a brown oil. Purification by flash chromatography (silica gel, EtOAc) afforded 251 mg (78%) of the desired product as a white solid. MS (ES+) m/z 319.0 [M+H]+.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous layer was extracted with EtOAc (50 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a brown oil
  6. customPurification by flash chromatography (silica gel, EtOAc)

Sources & evidence

ORD record
ord-64a4786a39fe40ad8e8a6e14b4c99d17
Source dataset
uspto-grants-2001_02
Patent number
US06191146B1

Reaction notes

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