6-Aminonicotinic acid → HCID 62074159, compound

HRID 2234430Notes

Reaction equation

HRID 2234430 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[NH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[O:8])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 184966-Aminonicotinic acidHCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 62074159HCID 62074159, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Aminonicotinic acid (Aldrich; 2 g, 14.48 mmol) and 4-amino-1-methylpiperidine (Fluorochem; 1.82 g, 15.92 g) were suspended in DMF (20 mL), DIPEA (7.5 mL, 43.44 mmol) and HATU (6.05 g, 15.92 mmol) were added and the reaction stirred at ambient temperature for 18 hrs. The solvent was evaporated and the residues stirred with water (50 mL for 1 hr filtered, acidified with 2M aq HCl and added to a 50 g SCX-2 column pre-wet with MeOH (2 column volumes). Flushed with MeOH (2 column volumes) then the crude product eluted with 2M ammonia in MeOH and evaporated. The residue was dissolved in DCM with a little MeOH to help solubility and purified on silica eluting with a gradient of 10-20% 2M ammonia in MeOH/DCM. Fractions containing product combined and evaporated to give the title compound as a cream solid (1.75 g, 52%)

Workup

  1. customThe solvent was evaporated
  2. stirringthe residues stirred with water (50 mL for 1 hr
  3. filtrationfiltered
  4. additionadded to a 50 g SCX-2 column pre-wet with MeOH (2 column volumes)
  5. customFlushed with MeOH (2 column volumes)
  6. washthe crude product eluted with 2M ammonia in MeOH
  7. customevaporated
  8. dissolutionThe residue was dissolved in DCM with a little MeOH
  9. custompurified on silica eluting with a gradient of 10-20% 2M ammonia in MeOH/DCM
  10. additionFractions containing product
  11. customevaporated

Sources & evidence

ORD record
ord-61ab8fd1fd064abaaa5de9d278f3e0f6
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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