Triethylamine → N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-isopropoxyethyl)benzamide

HRID 2170471Notes

Reaction equation

HRID 2170471 reaction equation
[CH:1]([O:4][CH:5]([C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1)[CH3:6])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH2:47][CH2:48][C:49]1[C:50]([OH:57])=[N:51][C:52]([CH3:56])=[CH:53][C:54]=1[CH3:55]>ClCCl.O>[OH:57][C:50]1[C:49]([CH2:48][NH:47][C:11](=[O:13])[C:10]2[CH:9]=[CH:8][C:7]([CH:5]([O:4][CH:1]([CH3:2])[CH3:3])[CH3:6])=[CH:15][CH:14]=2)=[C:54]([CH3:55])[CH:53]=[C:52]([CH3:56])[N:51]=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 895807134-(1-Isopropoxyethyl)benzoic acidHCID 178425242HCID 178425242, compound

Product 1

HCID 178425183N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-isopropoxyethyl)benzamideYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To the solution of 4-(1-isopropoxyethyl)benzoic acid (137 mg, 0.66 mmol) in dichloromethane (80 mL) was added o-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (380 mg, 1 mmol) and triethylamine (200 mg, 2 mmol). then the 3-(aminomethyl)-4,6-di methylpyridin-2-ol (100 mg, 0.66 mmol) was added, the solution was stirred at room temperature for 12 hours, water (80 mL) was added and washed 3 times, the organic layer was evaporated and purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-isopropoxyethyl)benzamide (57 mg, 91%) LRMS (M+H+) m/z: calcd: 342.19. found 342; 1H-NMR (300 MHz, CD3OD) 1H-NMR (300 MHz, CD3OD) δ 7.77 (d, J=8.4 Hz, 2H), 7.40 (d, J=8.4 Hz, 2H), 6.10 (s, 1H), 4.64-4.62 (m, 1H), 4.49 (s, 2H), 3.52-3.48 (m, 1H), 2.36 (s, 3H), 2.24 (s, 3H), 1.36 (d, J=6.3 Hz, 3H), 1.15 (d, J=6 Hz, 3H), 1.06 (d, J=6 Hz, 3H).

Workup

  1. washwashed 3 times
  2. customthe organic layer was evaporated
  3. custompurified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-e2e85e530f8e4a92b5d55966f1be4371
Source dataset
uspto-grants-2015_06
Patent number
US09051269B2

Reaction notes

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