Triethylamine → HCID 178448501, compound

HRID 1479760Notes

Reaction equation

HRID 1479760 reaction equation
[CH:1]([N:5]1[CH:10]=[CH:9][C:8]([C:11]([OH:13])=O)=[CH:7][C:6]1=[O:14])([CH2:3][CH3:4])[CH3:2].N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[NH2:44][CH2:45][C:46]1[C:47]([OH:54])=[N:48][C:49]([CH3:53])=[CH:50][C:51]=1[CH3:52]>ClCCl.O>[CH:1]([N:5]1[CH:10]=[CH:9][C:8]([C:11]([NH:44][CH2:45][C:46]2[C:47]([OH:54])=[N:48][C:49]([CH3:53])=[CH:50][C:51]=2[CH3:52])=[O:13])=[CH:7][C:6]1=[O:14])([CH2:3][CH3:4])[CH3:2]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89580764HCID 89580764, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178448501HCID 178448501, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-sec-butyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid (98 mg, 0.5 mmol) in dichloromethane (20 mL) were added 1H-benzo[d][1,2,3]triazol-1-ol (135 mg, 1 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (190 mg, 1 mmol) and triethylamine (253 mg, 2.5 mmol), and stirred at room temperature for 0.5 hour, 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (152 mg, 1 mmol) was added and stirred for 4 hours. To the reaction mixture was added water (20 mL), extracted with dichloromethane (20 mL) two times, combined and concentrated the organic layers, the residue was purified by chromatography with petroleum/ethyl acetate=1:1 to afford 1-sec-butyl-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-2-oxo-1,2-dihydropyridine-4-carboxamide (132 mg, 80% yield). LRMS (M+H+) m/z: calcd for 329.17. found 329. HPLC Purity (214 nm): 99%. 1H NMR (300 MHz, d6-DMSO): δ 11.48 (s, 1H), 8.54 (d, J=4.8 Hz, 1H), 7.71 (d, J=7.2 Hz, 1H), 6.84 (s, 1H), 6.53 (dd, J=1.8 and 7.2 Hz, 1H), 5.86 (s, 1H), 4.87-4.79 (m, 1H), 4.23 (d, J=4.8 Hz, 2H), 2.14 (s, 3H), 2.08 (s, 3H), 1.71-1.61 (m, 2H), 1.25 (d, J=6.9 Hz, 6H), 0.72 (t, J=7.2 Hz, 3H).

Workup

  1. stirringstirred for 4 hours
  2. extractionextracted with dichloromethane (20 mL) two times
  3. concentrationconcentrated the organic layers
  4. customthe residue was purified by chromatography with petroleum/ethyl acetate=1:1

Sources & evidence

ORD record
ord-b785dab56fb1479d861369de7f9a98b2
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Reaction notes

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