Triethylamine → HCID 178425205, compound

HRID 1501008Notes

Reaction equation

HRID 1501008 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH2:49][CH2:50][C:51]1[C:52]([OH:59])=[N:53][C:54]([CH3:58])=[CH:55][C:56]=1[CH3:57]>ClCCl>[OH:59][C:52]1[C:51]([CH2:50][NH:49][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][C:9]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][C:2]=2[CH3:1])=[C:56]([CH3:57])[CH:55]=[C:54]([CH3:58])[N:53]=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 621356342-Methyl-4-phenoxybenzoic acidHCID 178425242HCID 178425242, compound

Product 1

HCID 178425205HCID 178425205, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-4-phenoxybenzoic acid (100 mg, 0.44 mmol) in dichloromethane (20 mL) were added o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (190 mg, 0.5 mmol), and triethylamine (77 mg, 0.7 mmol). The mixture was stirred for 0.5 hour. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (60 mg, 0.4 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) to afford N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-2-methyl-4-phenoxybenzamide (40 mg, 25%) as a white solid. LRMS (M+H+) m/z: calcd 362.16. found 362. HPLC purity (214 nm): 100%. 1H NMR (300 MHz, d6-DMSO): δ 7.40-7.31 (m, 3H), 7.18-7.13 (m, 1H), 7.02-6.99 (m, 2H), 6.83-6.76 (m, 2H), 6.12 (s, 2H), 4.47 (s, 2H), 2.43 (s, 3H), 2.41 (s, 3H), 2.20 (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-1a89d91afdbb486d940c8ff15be3b748
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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