Trifluoroacetic acid → 3-(Tetrahydro-pyran-4-ylamino)-isonicotinic acid methyl ester

HRID 1256635Notes

Reaction equation

HRID 1256635 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[NH2:10].FC(F)(F)C(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[O:33]1[CH2:38][CH2:37][C:36](=O)[CH2:35][CH2:34]1.[Na]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[NH:10][CH:36]1[CH2:37][CH2:38][O:33][CH2:34][CH2:35]1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 1488824Methyl 3-aminopyridine-4-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 5360545Sodium

Product 1

HCID 667359013-(Tetrahydro-pyran-4-ylamino)-isonicotinic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-amino-isonicotinic acid methyl ester (500 mg, 3.29 mmol), dry N,N-dimethylformamide (10 mL), trifluoroacetic acid (1 mL) and sodium triacetoxyborohydride (1.4 g, 6.6 mmol, 2 eq) was added tetrahydro-pyran-4-one (0.5 mL, 4.94 mmol, 1.3 eq). The reaction mixture was stirred at room temperature for 24 hours then poured into saturated sodium hydrogenocarbonate (100 mL) and extracted with ethyl acetate (100 mL). The organic layer was dried over sodium sulfate and evaporated to dryness affording the crude title compound as yellow syrup that was used as such for the next step.

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-be130015b48c4a6e95ff0d4438436404
Source dataset
uspto-grants-2013_06
Patent number
US08461193B2

Reaction notes

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