Triethylamine → HCID 178425702, compound

HRID 1501168Notes

Reaction equation

HRID 1501168 reaction equation
O1[CH2:5][CH2:4][CH:3]([O:6][CH:7]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[CH3:8])[CH2:2]1.Cl.C(N=C=N[CH2:24][CH2:25][CH2:26]N(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[NH2:47][CH2:48][C:49]1[C:50]([OH:57])=[N:51][C:52]([CH3:56])=[CH:53][C:54]=1[CH3:55]>ClCCl>[OH:57][C:50]1[C:49]([CH2:48][NH:47][C:13](=[O:15])[C:12]2[CH:11]=[CH:10][C:9]([CH:7]([O:6][C:3]3[CH:2]=[C:25]([CH3:26])[CH:24]=[CH:5][CH:4]=3)[CH3:8])=[CH:17][CH:16]=2)=[C:54]([CH3:55])[CH:53]=[C:52]([CH3:56])[N:51]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89581015HCID 89581015, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425702HCID 178425702, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(1-(tetrahydrofuran-3-yloxy)ethyl)benzoic acid (311 mg, 1.32 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (380 mg, 1.98 mmol), N-hydroxybenzotriazole (267.3 mg, 1.98 mmol) and triethylamine (400 mg, 3.96 mmol) in dichloromethane (50 mL) was stirred for 30 minutes at room temperature. Then to the mixture, 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (200.64 mg, 1.32 mmol) was added. The resultant mixture was stirred at room temperature for 12 hours. Then the mixture was washed with water (30 mL×3). The organic layer was concentrated to give a residue and the residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-(m-tolyloxy)ethyl)benzamide (Compound I-82) (452 mg, 92%). LRMS (M+H+) m/z: calcd 370. found 370. 1H NMR (300 MHz, CD3OD): a 7.78 (d, J=8.4 Hz, 2H), 7.42-7.41 (m, 2H), 6.11 (s, 1H), 4.61-4.58 (m, 1H), 4.49 (s, 2H), 4.07-4.04 (m, 1H), 3.87-3.62 (m, 4H), 2.37 (s, 3H), 2.24 (s, 3H), 1.98-1.87 (m, 2H), 1.40-1.38 (m, 3H).

Workup

  1. washThen the mixture was washed with water (30 mL×3)
  2. concentrationThe organic layer was concentrated
  3. customto give a residue
  4. customthe residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-cca7f9caaf6a45d7952fc078f533099c
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

Loading…