Diisopropylethylamine → HCID 43610512, compound

HRID 1890281Notes

Reaction equation

HRID 1890281 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[NH2:12][CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.CCN(C(C)C)C(C)C>C(O)C>[Cl:11][C:4]1[N:3]=[C:2]([NH:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 852392,6-Dichloro-3-nitropyridineHCID 4192234-Aminotetrahydropyran

Product 1

HCID 43610512HCID 43610512, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
175 °C

Procedure

2,6-Dichloro-3-nitropyridine (0.222 g, 1.15 mmol), 4-aminotetrahydropyran (0.109 g, 1.08 mmol) and DIEA (0.300 mL, 1.72 mmol) were taken up in ethanol (3.0 mL) and heated to 175° C. for 15 minutes in a heavy walled sealed tube under microwave irradiation. The solvent was removed under reduced pressure and the residual solid was purified by preparative HPLC to give the title compound (0.186 g). LCMS m/z=258.3 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.60-1.75 (m, 2H), 2.8 (d, J=12.4 Hz, 2H), 3.60 (t, J=11.4 Hz, 2H), 4.02 (d, J=11.8 Hz, 2H), 4.30-4.45 (m, 1H), 6.63 (d, J=8.6 Hz, 1H), 8.29 (d, J=5.8 Hz, 1H), 8.35 (d, J=8.6 Hz, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residual solid was purified by preparative HPLC

Sources & evidence

ORD record
ord-5f5e7376eb0b479d9813d8e6d35eef79
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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