Triethylamine → HCID 178425230, compound

HRID 1501207Notes

Reaction equation

HRID 1501207 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][N:3]1[C@@H:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:12].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[NH2:38][CH2:39][C:40]1[C:41]([OH:48])=[N:42][C:43]([CH3:47])=[CH:44][C:45]=1[CH3:46]>ClCCl>[OH:48][C:41]1[C:40]([CH2:39][NH:38][C:8]([C:6]2[CH:5]=[CH:4][N:3]([C@@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH3:12])[C:2](=[O:1])[CH:7]=2)=[O:10])=[C:45]([CH3:46])[CH:44]=[C:43]([CH3:47])[N:42]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89585123(R)-2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylic acidHCID 178425242HCID 178425242, compound

Product 1

HCID 178425230HCID 178425230, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (R)-2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxylic acid (336 mg, 1.4 mmol), 1-hydroxybenzotriozole (373 mg, 2.8 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (531 mg, 2.8 mmol), triethylamine (1.0 mL) in dichloromethane (30 mL) was added 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (210 mg, 1.4 mmol). The reaction mixture was stirred at 0° C. for 13 hours. The mixture was washed with water (20 mL×2). The organic phase was dried over sodium sulfate and filtered. The filtrate was concentrated. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1) to give (R)—N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-2-oxo-1-(1-phenylethyl)-1,2-dihydropyridine-4-carboxamide as a white solid (360 mg, 68%). LRMS (M+H+) m/z: calcd 377.17. found 377. HPLC Purity (214 nm): 100%. 1H NMR (300 MHz, d6-DMSO): δ 11.44 (s, 1H), 8.53 (t, J=4.8 Hz, 1H), 7.66 (d, J=3.3 Hz, 1H), 7.38-7.26 (m, 5H), 6.78 (s, 1H), 6.51 (dd, J=1.8 Hz, J2=6.9 Hz, 1H), 6.13 (q, J=7.2 Hz, 1H), 5.84 (s, 1H), 4.22 (d, J=4.8 Hz, 2H), 2.13 (s, 3H), 2.10 (s, 3H), 1.68 (d, J=7.2 Hz, 3H).

Workup

  1. washThe mixture was washed with water (20 mL×2)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-278438fcd27d440c914517e1592664f9
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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