Picolinic acid → HCID 70247755, compound

HRID 636286

Reaction equation

HRID 636286 reaction equation
[C:1]1([CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH2:8])[CH:2]=1.[CH:11]1[CH:12]=[CH:13][C:14]2N(O)N=[N:17][C:15]=2[CH:16]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27](O)=[O:28].CN([P+]([O:40]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:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]([NH:8][CH2:7][C:3]1[CH:4]=[CH:5][CH:6]=[C:1]([CH2:9][NH:10][C:16](=[O:40])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][N:17]=2)[CH:2]=1)=[O:28]

Participants

9

Reactant 5

HCID 1018Picolinic acidHCID 5234Sodium ChlorideHCID 151331,3-BenzenedimethanamineHCID 757711-HydroxybenzotriazoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 70247755HCID 70247755, compoundYield 103.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1,3-xylylenediamine (132 uL, 1.00 mmol) in DMF (10 mL) was sequentially added IPr2NEt (1.75 mL, 10.0 mmol), HOBt (405 mg, 3.00 mmol), picolinic acid (370 mg, 3.00 mmol) and BOP reagent (1.33 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 359 mg of the desired product as a white solid. MS (ES+) m/z 347.2 [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-80ac522f774a415da7cfb328b872673e
Source dataset
uspto-grants-2001_02
Patent number
US06191146B1

Linked notes

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