Ammonia → 2-Amino-4,6-diisopropoxy-nicotinamide

HRID 591784Notes

Reaction equation

HRID 591784 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH:12]([CH3:14])[CH3:13])[CH:8]=[C:7]([O:15][CH:16]([CH3:18])[CH3:17])[C:3]=1[C:4](O)=[O:5].CC[N:21]=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.N>C1COCC1.O>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH:12]([CH3:14])[CH3:13])[CH:8]=[C:7]([O:15][CH:16]([CH3:18])[CH3:17])[C:3]=1[C:4]([NH2:21])=[O:5]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 666710672-Amino-4,6-diisopropoxy-nicotinic acid

Product 1

HCID 666709532-Amino-4,6-diisopropoxy-nicotinamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-4,6-diisopropoxy-nicotinic acid (1.48 g, 5.83 mmol) in THF (30 mL) were added EDCl (1.34 g, 6.99 mmol), HOBt (0.94 g, 6.99 mmol), NMM (0.70 g, 6.99 mmol) and liquid NH3 (10 mL). Then, the reaction mixture was stirred at room temperature for 24 hours. Then, water (100 mL) was added and the products were extracted with ethyl acetate (2×200 mL). The combined organic phase was washed with water, then brine, and dried over anhydrous Na2SO4. Removal of solvent gave crude 2-amino-4,6-diisopropoxy-nicotinamide as a yellow oil. Yield: 450 mg (26%, crude).

Workup

  1. extractionthe products were extracted with ethyl acetate (2×200 mL)
  2. washThe combined organic phase was washed with water
  3. dry with materialbrine, and dried over anhydrous Na2SO4
  4. customRemoval of solvent

Sources & evidence

ORD record
ord-1d81e4c8aef9485fae0c6d5828655a4b
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

Loading…