3-Aminopyridine → HCID 58154773, compound

HRID 2359430Notes

Reaction equation

HRID 2359430 reaction equation
[Cl:1][C:2]1[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][C:9]2[C:4](=[C:5]([C:16]([OH:18])=O)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1.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>C(Cl)Cl>[Cl:1][C:2]1[C:11]([C:12]([F:13])([F:14])[F:15])=[CH:10][C:9]2[C:4](=[C:5]([C:16]([NH:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[O:18])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

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 11033099HCID 11033099, compound

Product 1

HCID 58154773HCID 58154773, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-chloro-3-(trifluoromethyl)quinoline-8-carboxylic acid (165 mg, 0.60 mmol), 3-aminopyridine (73 mg, 0.78 mmol), HATU (365 mg, 0.96 mmol), DIPEA (312 mg, 2.4 mmol) in CH2Cl2 (4 ml) was stirred at room temperature under N2 overnight. The reaction mixture was washed with water (5 mL) and brine (3×5 mL). The organic solution was dried, concentrated, and purified by silica gel column chromatography (25% ethyl acetate in pentane to give 2-chloro-N-(pyridin-3-yl)-3-(trifluoromethyl)quinoline-8-carboxamide as a white solid. (36 mg 65% yield.)

Workup

  1. washThe reaction mixture was washed with water (5 mL) and brine (3×5 mL)
  2. customThe organic solution was dried
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography (25% ethyl acetate in pentane

Sources & evidence

ORD record
ord-a1b8b3835cb74d6ab106e03b23445f8b
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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