Triethylamine → HCID 178425193, compound

HRID 1501033Notes

Reaction equation

HRID 1501033 reaction equation
[CH3:1][N:2]([CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH2:50][CH2:51][C:52]1[C:53]([OH:60])=[N:54][C:55]([CH3:59])=[CH:56][C:57]=1[CH3:58]>ClCCl>[OH:60][C:53]1[C:52]([CH2:51][NH:50][C:14](=[O:16])[C:13]2[CH:12]=[CH:11][C:10]([CH2:9][N:2]([CH3:1])[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[CH:18][CH:17]=2)=[C:57]([CH3:58])[CH:56]=[C:55]([CH3:59])[N:54]=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 167745434-((Methyl(phenyl)amino)methyl)benzoic acidHCID 178425242HCID 178425242, compound

Product 1

HCID 178425193HCID 178425193, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-((methyl(phenyl)amino)methyl)benzoic acid (200 mg, 0.83 mmol) in dichloromethane (50 mL) were added o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (380 mg, 1 mmol) and triethylamine (202 mg, 2 mmol). The mixture was stirred for 0.5 hour. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (120 mg, 0.8 mmol) was added and the mixture was stirred at room temperature for 4 hours. The mixture was washed with water (50 mL) and the organic phase was separated, concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) and to afford N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-((methyl(phenyl)amino)methyl)benzamide (50 mg, 16%) as white solid. LRMS (M+H+) m/z: calcd 375.19. found 375. HPLC purity (214 nm): 96%. 1H NMR (300 MHz, CD3OD): δ 7.73 (d, J=8.4 Hz, 2H), 7.29 (d, J=8.1 Hz, 2H), 7.15-7.13 (m, 2H), 6.74-6.70 (m, 3H), 6.10 (s, 1H), 4.57 (s, 2H), 4.47 (s, 2H), 3.01 (s. 3H), 2.35 (s, 3H), 2.23 (s, 3H).

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. washThe mixture was washed with water (50 mL)
  3. customthe organic phase was separated
  4. concentrationconcentrated
  5. customto give a residue
  6. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-1916b745b35f4dc388532e8ad8da6a4a
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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