Triethylamine → HCID 178425702, compound

HRID 1501188Notes

Reaction equation

HRID 1501188 reaction equation
O1C[CH2:5][CH:4]([O:7][CH:8]([C:10]2[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=2)[CH3:9])[CH2:3][CH2:2]1.Cl.C(N=C=N[CH2:25][CH2:26][CH2:27]N(C)C)C.ON1C2C=CC=CC=2N=N1.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:14](=[O:15])[C:13]2[CH:17]=[CH:18][C:10]([CH:8]([O:7][C:4]3[CH:5]=[C:26]([CH3:25])[CH:27]=[CH:2][CH:3]=3)[CH3:9])=[CH:11][CH:12]=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 89580822HCID 89580822, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425702HCID 178425702, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(1-(tetrahydro-2H-pyran-4-yloxy)ethyl)benzoic acid (326 mg, 1.3 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 (411 mg, 82%). LRMS (M+H+) m/z: calcd 384.2. found 384.

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-ab9a78241fd24e1e8ceea40c4a629558
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

Loading…