Propylamine → HCID 78322292, compound

HRID 2272706Notes

Reaction equation

HRID 2272706 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[N:14]=[C:13]2[C:21]([O:23]CC)=O)=[CH:8][C:7]=1[F:26]>C(O)C>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[N:14]=[C:13]2[C:21]([NH:4][CH2:1][CH2:2][CH3:3])=[O:23])=[CH:8][C:7]=1[F:26]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 86730068HCID 86730068, compound

Product 1

HCID 78322292HCID 78322292, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

n-Propylamine (148 mg, 2.5 mol) was added to a solution of ethyl 3-(4-chloro-3-fluorophenyl)-3H-imidazo[4,5-b]pyridine-2-carboxylate (C13) (80 mg, 0.25 mmol) in ethanol (5 mL) and the reaction mixture was stirred at room temperature for 18 hours. After concentration under reduced pressure, the residue was purified by preparative thin layer chromatography on silica gel (Eluent: 1:1 petroleum ether/ethyl acetate) to provide the product as a pale yellow solid. Yield: 28 mg, 84 μmol, 34%. LCMS m/z 332.9 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.43 (dd, J=4.8, 1.4 Hz, 1H), 8.26 (dd, J=8.2, 1.5 Hz, 1H), 7.67 (dd, J=8.4, 8.2 Hz, 1H), 7.45-7.50 (m, 2H), 7.30 (ddd, J=8.5, 2.3, 1.2 Hz, 1H), 3.28-3.34 (m, 2H, assumed; partially obscured by solvent peak), 1.58-1.68 (m, 2H), 0.96 (t, J=7.4 Hz, 3H).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe residue was purified by preparative thin layer chromatography on silica gel (Eluent: 1:1 petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-665ac9a38f7644a782f40489f6d1193c
Source dataset
uspto-grants-2015_09
Patent number
US09120788B2

Reaction notes

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