Triethylamine → HCID 178425702, compound

HRID 1501042Notes

Reaction equation

HRID 1501042 reaction equation
[C:1]1(C)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)[CH3:9].[CH3:20]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.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>[OH:61][C:54]1[C:53]([CH2:52][NH:51][C:14](=[O:16])[C:13]2[CH:12]=[CH:11][C:10]([CH:8]([O:7][C:2]3[CH:1]=[C:6]([CH3:20])[CH:5]=[CH:4][CH:3]=3)[CH3:9])=[CH:18][CH:17]=2)=[C:58]([CH3:59])[CH:57]=[C:56]([CH3:60])[N:55]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89580748HCID 89580748, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425702HCID 178425702, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 4-(1-(o-tolyloxy)ethyl)benzoic acid (124 mg, 0.48 mmol) in dichloromethane (80 mL) was added o-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (274 mg, 0.72 mmol) and triethylamine (145 mg, 1.44 mmol). then the 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (73 mg, 0.48 mmol) was added, the solution was stirred at room temperature for 12 hours, then washed with water (50 mL*3), the organic layer was evaporated and purified by column chromatography (silica gel, dichloromethane/meth anol=20:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-(m-tolyloxy)ethyl)benzamide (57 mg, 30%). LRMS (M+H+) m/z: calcd: 390.19. found 390; 1H-NMR (300 MHz, CD3OD) δ 7.75 (d, J=8.4 Hz, 2H), 7.45 (d, J=8.4 Hz, 2H), 7.71-7.08 (m, 1H), 6.97-6.92 (m, 1H), 6.77-6.66 (m, 2H), 6.10 (s, 1H), 5.46-5.44 (m, 1H), 4.48 (s, 2H), 2.36 (s, 3H), 2.28 (s, 3H), 2.24 (s, 3H), 1.62 (d, J=6.3 Hz, 3H).

Workup

  1. washwashed with water (50 mL*3)
  2. customthe organic layer was evaporated
  3. custompurified by column chromatography (silica gel, dichloromethane/meth anol=20:1)

Sources & evidence

ORD record
ord-7bffb2567b2843fe83fb8283ef591574
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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