Triethylamine → HCID 178425151, compound

HRID 1501201Notes

Reaction equation

HRID 1501201 reaction equation
C[C:2]1[CH:10]=[C:9]([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.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:4](=[O:6])[C:3]2[CH:2]=[CH:10][C:9]([CH:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH3:12])=[CH:8][CH:7]=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 895814372-Methyl-4-(1-phenylethyl)benzoic acidHCID 178425242HCID 178425242, compound

Product 1

HCID 178425151HCID 178425151, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-methyl-4-(1-phenylethyl)benzoic acid (150 mg, 0.6 mmol) was dissolved in 20 mL dichloromethane, and then N-hydroxybenzotriazole (0.9 mmol, 100 mg), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.9 mmol, 200 mg), triethylamine (10.48 mmol, 3 mL) was added to the mixture. After the mixture was stirred at room temperature for 10 minute, 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (0.6 mmol, 90 mg) was added. The mixture was stirred at room temperature for 18 hours. Then washed with water (30 mL), extracted with dichloromethane (40 mL). The organic layer were concentrated and subjected to column chromatography (silica gel, dichloromethane/menthol=15/1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-phenylethyl)benzamide (150 mg, 90%). 1H NMR (300 MHz, CD3OD): δ 7.25-7.05 (m, 8H), 6.08 (s, 1H), 4.44 (s, 2H), 4.09 (m, 1H), 2.35 (s, 3H), 2.31 (s, 3H), 2.23 (s, 3H) 1.59 (d, J=8.4 Hz, 3H); LRMS (M+H+) m/z: calcd 374.20. found 374.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. washThen washed with water (30 mL)
  3. extractionextracted with dichloromethane (40 mL)
  4. concentrationThe organic layer were concentrated

Sources & evidence

ORD record
ord-62eb720879c242b0a599610edff40249
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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