Triethylamine → HCID 178482202, compound

HRID 1501270Notes

Reaction equation

HRID 1501270 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[NH2:46][CH2:47][C:48]1[C:49]([OH:57])=[N:50][C:51]([CH3:56])=[CH:52][C:53]=1[NH:54][CH3:55]>ClCCl.O>[OH:57][C:49]1[C:48]([CH2:47][NH:46][C:12](=[O:14])[C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:16][CH:15]=2)=[C:53]([NH:54][CH3:55])[CH:52]=[C:51]([CH3:56])[N:50]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 751824-Phenoxybenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178482201HCID 178482201, compound

Product 1

HCID 178482202HCID 178482202, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-phenoxybenzoic acid (54 mg, 0.25 mmol) in dichloromethane (15 mL) were added 1-Hydroxybenzotriazole (49 mg, 0.36 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (69 mg, 0.36 mmol) and triethylamine (73 mg, 0.72 mmol). The resulting solution was stirred at room temperature for 30 minutes. Then 3-(aminomethyl)-6-methyl-4-(methylamino) pyridin-2-ol (60 mg, 0.36 mmol) was added to the solution, and it was stirred at room temperature for 16 hours. Water (20 mL) was added to the mixture. It was extracted with dichloromethane (50 mL). The organic layer was concentrated to provide crude product which was purified by silica gel column chromatography with dichloromethane/methanol=10:1 to afford N-((2-hydroxy-6-methyl-4-(methylamino)pyridin-3-yl)methyl)-4-phenoxybenzamide (10 mg, 11% yield) as a white solid. LRMS (M+H+) m/z: calcd 364.16. found 364. HPLC Purity (214 nm): 98%. 1H NMR (300 MHz, CD3OD): δ 7.78-7.81 (d, J=8.7 Hz, 2H), 7.37-7.43 (m, 2H), 7.20 (d, J=7.5 Hz, 1H), 6.97-7.06 (m, 4H), 5.90 (s, 1H), 4.40 (s, 2H), 2.90 (s, 3H), 2.23 (s, 3H).

Workup

  1. stirringwas stirred at room temperature for 16 hours
  2. extractionIt was extracted with dichloromethane (50 mL)
  3. concentrationThe organic layer was concentrated
  4. customto provide crude product which
  5. customwas purified by silica gel column chromatography with dichloromethane/methanol=10:1

Sources & evidence

ORD record
ord-7be470967a314196ba78f7f970de2013
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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