Triethylamine → HCID 178425148, compound

HRID 1501172Notes

Reaction equation

HRID 1501172 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH2:46][CH2:47][C:48]1[C:49]([OH:56])=[N:50][C:51]([CH3:55])=[CH:52][C:53]=1[CH3:54]>ClCCl>[OH:56][C:49]1[C:48]([CH2:47][NH:46][C:10](=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([CH:2]3[CH2:3][CH2:4][CH2:5][O:1]3)=[CH:14][CH:13]=2)=[C:53]([CH3:54])[CH:52]=[C:51]([CH3:55])[N:50]=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 822764934-(tetrahydrofuran-2-yl)benzoic acidHCID 178425242HCID 178425242, compound

Product 1

HCID 178425148HCID 178425148, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(tetrahydrofuran-2-yl)benzoic acid (95 mg, 0.5 mmol) in dichloromethane (20 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). The organic phase was separated and concentrated to give a residue. The residue was purified through column chromatography (silica gel, dichloromethane/methanol=20:1) and to afford N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(tetrahydrofuran-2-yl)benzamide (35 mg, 21%) as a white solid. LRMS (M+H+) m/z: calcd 326.16. found 326.

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 through column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-667b5f6d7dd8434fbc0da31d7912a745
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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