Triethylamine → HCID 178425141, compound

HRID 1501085Notes

Reaction equation

HRID 1501085 reaction equation
[O:1]([CH:8]1[CH2:17][CH2:16][CH2:15][C:14]2[CH:13]=[C:12]([C:18]([OH:20])=O)[CH:11]=[CH:10][C:9]1=2)[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.[NH2:50][CH2:51][C:52]1[C:53]([OH:60])=[N:54][C:55]([CH3:59])=[CH:56][C:57]=1[CH3:58]>ClCCl>[OH:60][C:53]1[C:52]([CH2:51][NH:50][C:18]([C:12]2[CH:11]=[CH:10][C:9]3[CH:8]([O:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH2:17][CH2:16][CH2:15][C:14]=3[CH:13]=2)=[O:20])=[C:57]([CH3:58])[CH:56]=[C:55]([CH3:59])[N:54]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89581450HCID 89581450, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425141HCID 178425141, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-phenoxy-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid (0.032 g, 0.12 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.06 g, 0.3 mmol) and N-hydroxybenzotriazole (0.03 g, 0.22 mmol) in dichloromethane (10 mL) was added triethylamine (0.03 g, 0.3 mmol). The reaction mixture was stirred for 15 minutes at room temperature, then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (0.03 g, 0.2 mmol) was added. The reaction mixture was stirred at room temperature for 12 hours. After the reaction, the mixture was washed with water (10 mL×3). The organic phase was concentrated and the residue was purified by column chromatography (silica gel, dichloromethane/methanol=15:1) to give pure product N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-5-phenoxy-5,6,7,8-tetrahydronaphthalene-2-carboxamide (Compound I-52) as a white solid (0.031 g, 63%). LRMS (M+H+) m/z: calcd 402.19. found 402. 1H NMR (300 MHz, CD3OD): δ 7.59 (s, 1H), 7.57 (d, J=7.5 Hz, 1H), 7.37 (d, J=7.8 Hz, 1H), 7.28 (t, J=7.2 Hz, 2H), 7.02-6.92 (m, 3H), 6.10 (s, 1H), 5.43 (t, J=4.5 Hz, 1H), 4.48 (s, 2H), 2.90-2.82 (m, 2H), 2.37 (s, 3H), 2.24 (s, 3H), 2.08-1.83 (m, 4H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 12 hours
  2. customAfter the reaction
  3. washthe mixture was washed with water (10 mL×3)
  4. concentrationThe organic phase was concentrated
  5. customthe residue was purified by column chromatography (silica gel, dichloromethane/methanol=15:1)

Sources & evidence

ORD record
ord-8827a27efd14422dac846644066f5983
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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