Picolinic acid → HCID 10164025, compound

HRID 132579Notes

Reaction equation

HRID 132579 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(#N)C.[NH2:28][C:29]1[CH:56]=[CH:55][CH:54]=[CH:53][C:30]=1[O:31][CH2:32][C:33]([OH:52])([CH3:51])[CH2:34][N:35]1[CH2:40][CH2:39][CH:38]([N:41]2[C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=3[NH:43][C:42]2=[O:50])[CH2:37][CH2:36]1.[N:57]1[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[C:63](O)=[O:64].CCN(C(C)C)C(C)C>C1COCC1>[OH:52][C:33]([CH3:51])([CH2:34][N:35]1[CH2:36][CH2:37][CH:38]([N:41]2[C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=3[NH:43][C:42]2=[O:50])[CH2:39][CH2:40]1)[CH2:32][O:31][C:30]1[CH:53]=[CH:54][CH:55]=[CH:56][C:29]=1[NH:28][C:63]([C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][N:57]=1)=[O:64]

Participants

7

Reactant 5

HCID 1018Picolinic acidHCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69197184HCID 69197184, compound

Product 1

HCID 10164025HCID 10164025, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

HATU in acetonitrile (0.2 M, 0.375 ml, 0.075 mmol) was added to a solution of 1-{1-[3-(2-aminophenoxy)-2-hydroxy-2-methylpropyl]-4-piperidinyl}-1,3-dihydro-2H-benzimidazol-2-one (0.020 g, 0.05 mmol), 2-pyridinecarboxylic acid (0.006 g, 0.05 mmol) and Hünigs base (0.013 ml, 0.075 mmol) in THF (0.5 ml). After 0.5 h at 40° C. and 2 h at room temperature the reaction mixture was concentrated, and the residue purified on silica (dichloromethane-methanol, 12:1, containing 1% of NH4OH (25%)). Yield 20 mg of the title compound.

Workup

  1. concentration2 h at room temperature the reaction mixture was concentrated
  2. customthe residue purified on silica (dichloromethane-methanol, 12:1, containing 1% of NH4OH (25%))

Sources & evidence

ORD record
ord-d49d26facc2e4c6b8aaab2d135cf19c8
Source dataset
uspto-grants-2008_06
Patent number
US07388020B2

Reaction notes

Loading…