Triethylamine → HCID 178425191, compound

HRID 1501183Notes

Reaction equation

HRID 1501183 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)C)[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.[NH2:50][CH2:51][C:52]1[C:53]([OH:60])=[N:54][C:55]([CH3:59])=[CH:56][C:57]=1[CH3:58]>ClCCl>[OH:60][C:53]1[C:52]([CH2:51][NH:50][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][C:9]([CH2:11][N:13]3[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]3)=[CH:10][C:2]=2[CH3:1])=[C:57]([CH3:58])[CH:56]=[C:55]([CH3:59])[N:54]=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 89585116HCID 89585116, 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-(1-(piperidin-1-yl)ethyl)benzoic acid (100 mg, 0.40 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) and 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. The residue was purified by preparative-TLC (silica gel, methanol/dichloromethane=1:15, 1% NH4OH) to afford N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-2-methyl-4-(piperidin-1-ylmethyl)benzamide as a white solid (35 mg, 23%). LRMS (M+H+) m/z: calcd 381.51. found 381. HPLC purity (214 nm): 93%. 1H NMR (300 MHz, CD3OD): δ 7.42-7.32 (m, 3H), 6.11 (s, 1H), 4.85 (s, 2H), 4.79-4.72 (m, 1H), 2.94-2.79 (m, 4H), 2.40 (s, 3H), 2.34 (s, 3H), 2.24 (s, 3H), 1.83-1.63 (m, 9H).

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. customThe residue was purified by preparative-TLC (silica gel, methanol/dichloromethane=1:15, 1% NH4OH)

Sources & evidence

ORD record
ord-be89bc25895b452d960587b70937478d
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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