Triethylamine → HCID 178436442, compound

HRID 1500980Notes

Reaction equation

HRID 1500980 reaction equation
[C:1]([C:3]1[C:19]([CH2:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:4]=1[O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][C:7]=1[CH3:15])#[N:2].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[NH2:51][CH2:52][C:53]1[C:54]([OH:61])=[N:55][C:56]([CH3:60])=[CH:57][C:58]=1[CH3:59]>ClCCl>[C:1]([C:3]1[C:19]([CH2:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:4]=1[O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH:51][CH2:52][C:53]2[C:54]([OH:61])=[N:55][C:56]([CH3:60])=[CH:57][C:58]=2[CH3:59])=[O:12])=[CH:8][C:7]=1[CH3:15])#[N:2]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89581315HCID 89581315, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178436442HCID 178436442, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-cyano-3-ethylphenoxy)-3-methylbenzoic acid (0.10 g, 0.36 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.10 g, 0.5 mmol) and N-hydroxybenzotriazole (0.07 g, 0.5 mmol) in dichloromethane (20 mL) was added triethylamine (0.4 g, 4 mmol). The reaction mixture was stirred at room temperature for 15 minutes, then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (0.06 g, 0.4 mmol) was added. The reaction mixture was stirred at room temperature for 12 hours. After the reaction, the mixture was washed with water (30 mL). The organic phase was concentrated and purified by column chromatography (silica gel, dichloromethane/methanol=15:1) to give pure product 4-(2-cyano-3-ethylphenoxy)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-3-methylbenzamide as a white solid (0.062 g, 41%). LRMS (M+H+) m/z: calcd 415.19. found 415. 1H NMR (300 MHz, d6-DMSO): δ 11.46 (s, 1H), 8.31 (d, J=4.5 Hz, 1H), 7.86 (s, 1H), 7.75 (s, 1H), 7.72 (s, 1H), 7.05-6.70 (m, 2H), 6.80 (dd, J=8.4 Hz, J=2.4 Hz, 1H), 5.85 (s, 1H), 4.29 (d, J=4.5 Hz, 2H), 2.74 (q, J=7.5 Hz, 2H), 2.16 (s, 3H), 2.14 (s, 3H), 2.10 (s, 3H), 1.17 (t, J=7.5 Hz, 3H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 12 hours
  2. customAfter the reaction
  3. washthe mixture was washed with water (30 mL)
  4. concentrationThe organic phase was concentrated
  5. custompurified by column chromatography (silica gel, dichloromethane/methanol=15:1)

Sources & evidence

ORD record
ord-763fede0af77482c84dd0da1ccadce88
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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