Picolinic acid → HCID 11496934, compound

HRID 130484Notes

Reaction equation

HRID 130484 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[SH:43][CH2:44][C:45]([C:47]1[CH:52]=[CH:51][C:50]([NH:53][S:54]([C:57]2[CH:62]=[CH:61][C:60]([O:63][C:64]([F:67])([F:66])[F:65])=[CH:59][CH:58]=2)(=[O:56])=[O:55])=[CH:49][CH:48]=1)=[O:46]>C(Cl)Cl>[O:46]=[C:45]([C:47]1[CH:52]=[CH:51][C:50]([NH:53][S:54]([C:57]2[CH:62]=[CH:61][C:60]([O:63][C:64]([F:67])([F:65])[F:66])=[CH:59][CH:58]=2)(=[O:56])=[O:55])=[CH:49][CH:48]=1)[CH2:44][S:43][C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:9]

Participants

6

Reactant 4

HCID 1018Picolinic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11165239HCID 11165239, compound

Product 1

HCID 11496934HCID 11496934, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Picolinic acid (0.25 g, 2.04 mmol) was dissolved in anhydrous, degassed DCM (5 ml), HATU (775 mg, 2.04 mmol) was added followed by DIEA (0.53 g, 4.1 mmol). The mixture was stirred for 20 min and N-[4-(2-Mercapto-acetyl)-phenyl]-4-trifluoromethoxy-benzenesulfonamide SII-4 (0.725 g, 1.85 mmol) was added in 5 ml anhydrous, degassed DCM and the mixture was stirred for 16 hours. The reaction was filtered and the solvent evaporated. The product was purified by flash chromatography (1:1 EtOAc:hexanes) to afford 125 mg (0.25 mmol, 14%) product as a white solid. 1H-NMR: (400 MHz, DMSO): 11.12 (s, 1H), 8.89 (d, 1H), 8.03 (t, 1H), 8.01 (d, 2H), 8.00 (d, 2H), 7.90 (d, 1H), 7.78 (t, 1H), 7.60 (d, 2H), 7.14 (d, 2H), 4.60 (s, 2H); LC-MS (ES+): 497 [MH]+ m/e.

Workup

  1. additionwas added
  2. customdegassed DCM
  3. stirringthe mixture was stirred for 16 hours
  4. filtrationThe reaction was filtered
  5. customthe solvent evaporated
  6. customThe product was purified by flash chromatography (1:1 EtOAc:hexanes)

Sources & evidence

ORD record
ord-b4810656ea54401591f2a9688fb4764c
Source dataset
uspto-grants-2008_06
Patent number
US07381749B2

Reaction notes

Loading…