Triethylamine → HCID 86640698, compound

HRID 2176169Notes

Reaction equation

HRID 2176169 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18]Cl)=[CH:14][N:13]=1.C(N(CC)CC)C>C(O)C>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:9]([C:6]2[CH:7]=[CH:8][C:3]([F:2])=[CH:4][CH:5]=2)[NH2:10])=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 86640698HCID 86640698, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (4-fluorophenyl)hydrazine hydrochloride (2.52 g, 20 mmol; Aldrich) and 2-chloro-5-(chloromethyl)pyridine (3.24 g, 20.00 mmol; Aldrich) in ethanol (120 mL) was treated with triethylamine (9.76 mL, 70.0 mmol; Aldrich), and the mixture was heated at 80° C. with stirring for 16 hours. The solvent was removed and the residue was purified by flash chromatography (silica gel, 10:1 CH2Cl2—CH3OH) to afford the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 4.53 (s, 2H), 6.93-6.99 (m, 2H), 7.02-7.10 (m, 2H), 7.40 (d, J=8 Hz, 1H), 7.77 (dd, J=8, 3 Hz, 1H), 8.30 (d, J=3 Hz, 1H); MS (DCI/NH3) m/z 252 (M+H)+.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by flash chromatography (silica gel, 10:1 CH2Cl2—CH3OH)

Sources & evidence

ORD record
ord-4283b36b1bb848fcb1a3ec37e7934724
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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