3-Aminopyridine → HCID 44555108, compound

HRID 2359406Notes

Reaction equation

HRID 2359406 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([C:20](O)=[O:21])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH:7]=[CH:8][CH:9]=1.CN(C(ON1N=[N:40][C:35]2[CH:36]=[CH:37][CH:38]=[N:39][C:34]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.NC1C=NC=CC=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[N:39]1[CH:38]=[CH:37][CH:36]=[C:35]([NH:40][C:20]([C:13]2[CH:14]=[CH:15][CH:16]=[C:17]3[C:12]=2[N:11]=[C:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:24])([F:23])[F:1])[CH:5]=2)[CH:19]=[CH:18]3)=[O:21])[CH:34]=1

Participants

7

Reactant 4

HCID 100093-AminopyridineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58154631HCID 58154631, compound

Product 1

HCID 44555108HCID 44555108, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-(3-(trifluoromethoxy)phenyl)quinoline-8-carboxylic acid (1 gram, 3.3 mmol) and HATU (1.71 g, 4.5 mmol) in DMF (30 mL) was added 3-aminopyridine (423 mg, 4.5 mmol) followed by DIPEA (1.03 mL, 6 mmol). The mixture was stirred 18 hours, water (150 mL) was added and the resulting precipitate was collected by filtration. The crude material was purified by chromatography (silica gel, gradient 0 to 100% Ethyl acetate in Pentane), the desired fraction was concentrated and the product recrystallized from methanol to obtain the product as a white solid (550 mg, 45% yield).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customThe crude material was purified by chromatography (silica gel, gradient 0 to 100% Ethyl acetate in Pentane)
  3. concentrationthe desired fraction was concentrated
  4. customthe product recrystallized from methanol

Sources & evidence

ORD record
ord-224ca95c5a304f55a910cf4ea0684023
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

Loading…