Triethylamine → HCID 178425152, compound

HRID 1501070Notes

Reaction equation

HRID 1501070 reaction equation
[CH2:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=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]([CH2:1][CH2:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[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 104894314-(2-Phenylethyl)benzoic acidHCID 178425242HCID 178425242, compound

Product 1

HCID 178425152HCID 178425152, compoundYield 21.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

4-Phenethylbenzoic acid (30 mg, 0.13 mmol), 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (103 mg, 0.27 mmol) was dissolved in dichloromethane (20 mL), and then added triethylamine (2 mL) was added. After the mixture were stirred at 25° C. for 0.5 hour, 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (20 mg, 0.13 mmol) was added. The mixture was stirred at 25° C. for 12 hours. To the mixture, water (15 ml) was added. 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 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-phenethylbenzamide (10 mg, 21%). LRMS (M+H+) m/z: calcd 360.18. found 360. HPLC purity (214 nm): 94%. 1H NMR (300 MHz, CD3OD): δ 7.67 (d, J=8.7 Hz, 2H), 7.24-7.12 (m, 7H), 6.10 (s, 1H), 4.48 (s, 2H), 2.95-2.91 (m, 4H), 2.36 (s, 3H), 2.24 (s, 3H).

Workup

  1. stirringThe mixture was stirred 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 in vacuo
  7. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-d8788bf61cef49cab0032ce16a375e93
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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