Triethylamine → HCID 178458283, compound

HRID 1501058Notes

Reaction equation

HRID 1501058 reaction equation
[O:1]([CH:8]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1)[CH2:9][CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][N:21](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.N[CH2:52][C:53]1[C:54]([OH:61])=[N:55][C:56]([CH3:60])=[CH:57][C:58]=1[CH3:59]>ClCCl>[OH:61][C:54]1[C:53]([CH2:52][CH2:20][NH:21][C:15](=[O:17])[C:14]2[CH:13]=[CH:12][C:11]([CH:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:9][CH3:10])=[CH:19][CH:18]=2)=[C:58]([CH3:59])[CH:57]=[C:56]([CH3:60])[N:55]=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 89581007HCID 89581007, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178458283HCID 178458283, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-(1-phenoxypropyl)benzoic acid (256 mg, 1.0 mmol), o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (570 mg, 1.5 mmol), triethylamine (0.45 mL) and dichloromethane (15 mL) were stirred at 25° C. for half an hour. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (152 mg, 1.0 mmol) was added. The mixture was stirred at 25° C. for 12 hours. The mixture was washed with water (20 mL), dried over sodium, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)ethyl)-4-(1-phenoxypropyl)benzamide (Compound I-44) as a white solid (125 mg, 32%). LRMS (M+H+) m/z: calcd 390.19. found 390. HPLC purity (214 nm): 95%. 1H NMR (300 MHz, d6-DMSO): δ 11.44 (s, 1H), 8.28 (t, J=5.1 Hz, 1H), 7.78 (d, J=8.4 Hz, 2H), 7.42 (d, J=8.4 Hz, 2H), 7.17 (t, J=8.0 Hz, 2H), 6.87-6.83 (m, 3H), 5.84 (s, 1H), 5.27 (t, J=6.0 Hz, 1H), 4.27 (d, J=5.1 Hz, 2H), 2.68 (s, 3H), 2.51 (s, 3H), 1.89-1.80 (m, 2H), 0.92 (t, J=6.6 Hz, 3H).

Workup

  1. stirringThe mixture was stirred at 25° C. for 12 hours
  2. washThe mixture was washed with water (20 mL)
  3. dry with materialdried over sodium
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue
  7. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-78aec88ff48b484c9aabe08efa8aba99
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

Loading…