Triethylamine → HCID 178425172, compound

HRID 1501112Notes

Reaction equation

HRID 1501112 reaction equation
[O:1]([CH:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][N:11]=1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[NH2:48][CH2:49][C:50]1[C:51]([OH:58])=[N:52][C:53]([CH3:57])=[CH:54][C:55]=1[CH3:56]>ClCCl>[OH:58][C:51]1[C:50]([CH2:49][NH:48][C:14](=[O:16])[C:13]2[CH:17]=[CH:18][C:10]([CH:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH3:9])=[N:11][CH:12]=2)=[C:55]([CH3:56])[CH:54]=[C:53]([CH3:57])[N:52]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89581384HCID 89581384, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425172HCID 178425172, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(1-phenoxyethyl)nicotinic acid (100 mg, 0.41 mmol) in dichloromethane (20 mL) were added N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (115 mg, 0.60 mmol), N-hydroxybenzotriazole (81 mg, 0.60 mmol) and triethylamine (122 mg, 1.20 mmol). The resultant reaction mixture was stirred for 30 minutes at room temperature. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (76 mg, 0.50 mmol) was added and the mixture was stirred at ambient temperature overnight. The mixture was washed with brine (20 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified through pre-HPLC and the obtained solution was freeze-dried to afford N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-6-(1-phenoxyethyl)nicotinamide (50 mg, 32.2%) as a white solid. LRMS (M+H+) m/z: calcd 378.17. found 378. 1H NMR (300 MHz, DMSO) δ 8.91 (d, J=2.1 Hz, 1H), 8.14 (dd, J1=8.1 Hz, J2=2.1 Hz, 1H), 7.55 (d, J=8.1 Hz, 1H), 7.17 (m, 2H), 6.85 (m, 3H), 6.10 (s, 1H), 5.45 (m, 1H), 4.48 (s, 2H), 2.35 (s, 3H), 2.24 (s, 3H), 1.64 (d, J=6.6 Hz, 3H).

Workup

  1. customThe resultant reaction mixture
  2. stirringthe mixture was stirred at ambient temperature overnight
  3. washThe mixture was washed with brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified through pre-HPLC and the obtained solution
  8. customwas freeze-dried

Sources & evidence

ORD record
ord-03f0fc9f861e4e7c83afcd7564c5530c
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

Loading…