Picolinic acid → HCID 10917831, compound

HRID 636288Notes

Reaction equation

HRID 636288 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].CCN(C(C)C)C(C)C.[CH:18]1[CH:19]=[CH:20][C:21]2N(O)N=[N:24][C:22]=2[CH:23]=1.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34](O)=[O:35].CN([P+]([O:47]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:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]([NH:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[NH:8][C:23](=[O:47])[C:22]1[CH:21]=[CH:20][CH:19]=[CH:18][N:24]=1)=[O:35]

Participants

10

Reactant 6

HCID 1018Picolinic acidHCID 5234Sodium ChlorideHCID 7243O-PhenylenediamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 10917831HCID 10917831, compoundYield 94.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1,2-phenylenediamine (111 mg, 1.00 mmol) in DMF (10 mL) was sequentially added iPr2NEt (1.75 mL, 10.0 mmol), HOBt (406 mg, 3.00 mmol), picolinic acid (370 mg, 3.00 mmol), and BOP reagent (1.34 g, 3.00 mmol). 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 302 mg (92%) 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-c783a9de414e48109bbea399c97b293a
Source dataset
uspto-grants-2001_02
Patent number
US06191146B1

Reaction notes

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