Dimethylamine → 6-amino-N,N-dimethylpyridine-3-carboxamide

HRID 1098149Notes

Reaction equation

HRID 1098149 reaction equation
[CH2:1]([N:3](C(C)C)[CH:4](C)C)C.[NH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][N:12]=1.CNC.CCN=C=NCCCN(C)C>C1COCC1>[NH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([N:3]([CH3:4])[CH3:1])=[O:16])=[CH:13][N:12]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 184966-Aminonicotinic acidHCID 81531Diisopropylethylamine

Product 1

HCID 575045326-amino-N,N-dimethylpyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Ethyl-N-isopropylpropan-2-amine (12.61 mL, 72.40 mmol) was added to 6-aminonicotinic acid (CAS no. 3167-49-5) (5 g, 36.20 mmol), dimethylamine (2M in THF) (21.72 mL, 43.44 mmol) and EDCI (9.02 g, 47.06 mmol) in THF (150 mL) under nitrogen. The resulting suspension was stirred at r.t. for 18 hours. The reaction mixture was dry loaded onto silica and purified by flash silica chromatography, eluting with 0 to 10% MeOH in ethyl acetate to the product (4.50 g, 75%). 1H NMR (400 MHz, DMSO) δ 2.95 (6H, s), 6.28 (2H, s), 6.38-6.44 (1H, m), 7.42-7.47 (1H, m), 7.99-8.04 (1H, m)

Workup

  1. customThe reaction mixture was dry
  2. custompurified by flash silica chromatography
  3. washeluting with 0 to 10% MeOH in ethyl acetate to the product (4.50 g, 75%)

Sources & evidence

ORD record
ord-199b0f91fdd8460ab0ffa507351a26d2
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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