Ethanol → HCID 178515771, compound

HRID 1890287Notes

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.NC1C[CH2:17][CH:16]([OH:19])[CH2:15]C1.CC[N:22]([CH:26]([CH3:28])[CH3:27])[CH:23](C)C.C([OH:31])C>>[OH:19][CH:16]1[CH2:17][CH2:27][CH:26]([N:22]2[C:2]3=[N:3][C:4]([OH:31])=[CH:5][CH:6]=[C:7]3[N:8]=[CH:23]2)[CH2:28][CH2:15]1

Participants

Reactant 4

HCID 702Ethanol

HCID 812934-Aminocyclohexanol

HCID 81531Diisopropylethylamine

HCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 178515771HCID 178515771, compound

Procedure

2,6-Dichloro-3-nitropyridine (0.500 g, 2.59 mmol), 4-aminocyclohexanol (0.298 g, 2.59 mmol), DIEA (1.00 ml, 5.73 mmol) and ethanol (2.0 ml) were heated to 80° C. for 18 h in a sealed flask. The solvent was removed under reduced pressure and the residual solid was purified by preparative HPLC to give the title compound (0.894 g). LCMS m/z=272.2 [M+H]+; 1H NMR (400 MHz, acetonitrile-d3) δ ppm 1.3-1.52 (m, 4H), 2.0-2.1 (m, 2H), 2.15-2.2 (m, 2H), 2.74 (br s, 1H), 6.67 (d, J=8.6 Hz, 1H), 8.16 (br s, 1H), 8.36 (d, J=8.6 Hz, 1H).

Workup

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

Sources & evidence

ORD record: ord-bac54b8153ab455cb1acbf2f16fe6618
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507473B2

Reaction notes

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