Triethylamine → HCID 178425191, compound

HRID 1501166Notes

Reaction equation

HRID 1501166 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH2:11][N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.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>[OH:59][C:52]1[C:51]([CH2:50][NH:49][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)=[CH:10][C:2]=2[CH3:1])=[C:56]([CH3:57])[CH:55]=[C:54]([CH3:58])[N:53]=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 89581234HCID 89581234, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425191HCID 178425191, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methyl-4-(piperidin-1-ylmethyl)benzoic acid (100 mg, 0.43 mmol) in dichloromethane (50 mL) was added 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (35 mg, 0.1 mmol), triethylamine (32 mg, 0.3 mmol). The mixture was stirred for 30 minutes. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (27 mg, 0.2 mmol) was added and the mixture was stirred at room temperature for 12 hours. The mixture was washed with water (50 mL), dried over sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to afford N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-2-methyl-4-(piperidin-1-ylmethyl)benzamide as white solid (35 mg, 19%). LRMS (M+H+) m/z: calcd 367.23. found 367. HPLC purity (214 nm): 96%. 1H NMR (300 MHz, CD3OD): δ 7.54-7.46 (m, 3H), 6.26 (s, 1H), 4.62 (s, 2H), 4.17 (s, 2H), 3.10 (s, 4H), 2.54 (s, 3H), 2.53 (s, 3H), 2.39 (s, 3H), 1.93-1.89 (m, 4H), 1.77-1.75 (m, 2H).

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. washThe mixture was washed with water (50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue
  7. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-17b373e6b3aa4194b53d01ce25c30643
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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