Triethylamine → HCID 24967277, compound

HRID 1666498Notes

Reaction equation

HRID 1666498 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=[C:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH:11]=2)[CH:4]=1.C1([O:29][C:30](=O)[NH:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)C=CC=CC=1.NC1C=NC=CC=1.C(N(CC)CC)C>C(#N)C>[CH3:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([O:9][C:10]2[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=2)[CH:16]=[C:17]2[CH2:22][CH2:21][N:20]([C:30]([NH:31][C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)=[O:29])[CH2:19][CH2:18]2)[CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 66876955HCID 66876955, compound

Product 1

HCID 24967277HCID 24967277, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Methyl-2-(3-piperidin-4-ylidenemethyl-phenoxy)-pyridine hydrochloride (530 mg, 1.5 mmol, from Step 5), pyridin-3-yl-carbamic acid phenyl ester (402 mg, 1.88 mmol, prepared according to the procedure described in Synthesis, 1997, 1189-1194 from 3-aminopyridine) and triethylamine (0.836 mL, 6.0 mmol) were combined in acetonitrile (10 mL) and stirred at room temperature. After 16 hours, the reaction was concentrated forming a residue and the residue was partitioned between EtOAc and water. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (0-5%, (8:1 EtOH:conc. NH4OH):DCM) to afford the desired product (429 mg) as a foamy white solid. MS (APCI 10V) AP+ 401.4, 281.2 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.35 (s, 3H) 2.45 (td, J=5.82, 0.99 Hz, 2H) 2.57 (td, J=5.81, 1.11 Hz, 2H) 3.51-3.57 (m, 2H) 3.61-3.67 (m, 2H) 6.44 (s, 1H) 6.73-6.80 (m, 1H) 6.90-6.95 (m, 2H) 6.97 (dt, J=5.18, 0.61 Hz, 1H) 7.08 (d, J=8.02 Hz, 1H) 7.30-7.42 (m, 2H) 7.91 (ddd, J=8.38, 2.58, 1.45 Hz, 1H) 7.98 (d, J=5.24 Hz, 1H) 8.16 (dd, J=4.81, 1.40 Hz, 1H) 8.58 (d, J=2.51 Hz, 1H)

Workup

  1. concentrationthe reaction was concentrated
  2. customforming a residue
  3. customthe residue was partitioned between EtOAc and water
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (0-5%, (8:1 EtOH:conc. NH4OH):DCM)

Sources & evidence

ORD record
ord-4b7f4be655c94ade9e53fdceee5bba48
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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