Triethylamine → HCID 178425151, compound

HRID 1501026Notes

Reaction equation

HRID 1501026 reaction equation
[C:1]1([CH:7]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.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.O>[OH:59][C:52]1[C:51]([CH2:50][NH:49][C:13](=[O:15])[C:12]2[CH:11]=[CH:10][C:9]([CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH3:8])=[CH:17][CH:16]=2)=[C:56]([CH3:57])[CH:55]=[C:54]([CH3:58])[N:53]=1

Participants

7

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 195999744-(1-Phenylethyl)benzoic acidHCID 178425242HCID 178425242, compound

Product 1

HCID 178425151HCID 178425151, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-(1-phenylethyl)benzoic acid (150 mg, 0.66 mol), 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (303 mg, 0.797 mmol), triethylamine (2 mL) in dichloromethane (25 mL) was stirred at 25° C. for 0.5 hour. And then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (101 mg, 0.66 mmol) was added. After stirring at 25° C. for 12 hours, water (15 mL) was added to the reaction mixture. And the mixture was extracted with dichloromethane (10 mL×3). The combined organic phase was separated, dried by sodium sulfate and then filtered. The filtrate was concentrated to give a residue in vacuo. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-phenylethyl)benzamide (100 mg, 42%).

Workup

  1. stirringAfter stirring at 25° C. for 12 hours
  2. extractionAnd the mixture was extracted with dichloromethane (10 mL×3)
  3. customThe combined organic phase was separated
  4. dry with materialdried by sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customto give a residue in vacuo
  8. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-d34d3ee2d0a04434ab0ee6cd16f7ef91
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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