Picolinic acid → HCID 9951363, compound

HRID 636284Notes

Reaction equation

HRID 636284 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.CN([P+](ON1N=[N:28][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27]C1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[CH:37]1[CH:38]=[CH:39][C:40]2N(O)N=[N:43][C:41]=2[CH:42]=1.C(N(C(C)C)[CH:50]([CH3:52])[CH3:51])C.[CH3:56][N:57]([CH:59]=[O:60])C>>[N:28]1[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=1[C:59]([NH:57][CH:56]1[C:39]2[C:38](=[CH:37][CH:42]=[C:41]([NH:43][C:7](=[O:9])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH:40]=2)[CH2:52][CH2:50][CH2:51]1)=[O:60]

Participants

6

Reactant 5

HCID 1018Picolinic acidHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 9951363HCID 9951363, compound

Procedure

The compound of Example 1(c) (0.95 g, 5.8 mmol) was dissolved in DMF (10 mL) and was treated at 0° C. with picolinic acid (2.14 g, 17.4 mmol), Bop reagent (7.70 g, 17.4 mmol), HOBt (2.35 g, 17.4 mmol) and iPr2EtN (10.1 mL, 58.0 mmol). After 20 h at RT, the solvent was evaporated under high vacuum. The residue was dissolved in CHCl3 and washed with 1 N HCl. Removal of solvent under reduced pressure gave crude product which was purified by flash chromatography (silica gel, 40% EtOAc in hexane) to give 430 mg of the desired material. This material was further recrystallized from CHCl3:EtOAc:Hexane (3:1:1) to give 230 mg of pure material. MS (ES+) m/z 373 [M+H]+.

Workup

  1. customthe solvent was evaporated under high vacuum
  2. dissolutionThe residue was dissolved in CHCl3
  3. washwashed with 1 N HCl
  4. customRemoval of solvent under reduced pressure
  5. customgave crude product which
  6. customwas purified by flash chromatography (silica gel, 40% EtOAc in hexane)

Sources & evidence

ORD record
ord-71002238e05941c4857f0c94d0a62146
Source dataset
uspto-grants-2001_02
Patent number
US06191146B1

Reaction notes

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