2-Aminopyridine → HCID 25120171, compound

HRID 1893483Notes

Reaction equation

HRID 1893483 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:7]2[N:8]([CH:22]=[CH:23][N:24]=2)[C:9]2[C:14]([N:15]=1)=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[C:11]([CH:20]=O)[CH:10]=2.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.[BH4-].[Na+]>O1CCCC1.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[N:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[NH:25][CH2:20][C:11]1[CH:10]=[C:9]2[C:14]([N:15]=[C:6]([NH:5][CH2:4][CH2:3][CH2:2][OH:1])[C:7]3[N:8]2[CH:22]=[CH:23][N:24]=3)=[CH:13][C:12]=1[C:16]([F:17])([F:18])[F:19]

Participants

6

Reactant 3

HCID 104392-AminopyridineHCID 4311764Sodium borohydrideHCID 59333301HCID 59333301, compound

Product 1

HCID 25120171HCID 25120171, compoundYield 25.7%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[(3-hydroxypropyl)amino]-7-(trifluoromethyl)imidazo[1,2-a]quinoxaline-8-carbaldehyde (25 mg; 0.07 mmol; 1 eq), 2-aminopyridine (20 mg; 0.21 mmol; 3 eq) and titanium tetraisopropoxide (60 mg; 0.21 mg; 3 eq) in anhydrous tetrahydrofuran (0.2 ml) with a few 4A molecular sieves stirred under Ar at rt for 5 h is added sodium borohydride (3 mg; 0.07 mmol; 1 eq). The resulting reaction mixture is then stirred under Ar at rt for 16 h. Partition (aqueous ammonium chloride/ethyl acetate), filtration over Celite, extraction of the aqueous phase (ethyl acetate), reunion of the organic phases, drying (magnesium sulphate) and purification by prep CCM on silicagel (dichloromethane/methanol 95:5) affords the title product (7.4 mg; 0.018 mmol; 25%).

Workup

  1. customThe resulting reaction mixture
  2. customPartition
  3. filtration(aqueous ammonium chloride/ethyl acetate), filtration
  4. extractionover Celite, extraction of the aqueous phase (ethyl acetate), reunion of the organic phases
  5. customdrying
  6. custom(magnesium sulphate) and purification by prep CCM on silicagel (dichloromethane/methanol 95:5)

Sources & evidence

ORD record
ord-cda8a5d5aba440f8af45ceae4d84a3e0
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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