ChemicalBook CAS DataBase List 1-Cyclopropyl-1,3-dihydroimidazo[4,5-c]pyridine-2-one

1-Cyclopropyl-1,3-dihydroimidazo[4,5-c]pyridine-2-one synthesis

8synthesis methods

Product Name:1-Cyclopropyl-1,3-dihydroimidazo[4,5-c]pyridine-2-one
CAS Number:380605-29-8
Molecular formula:C9H9N3O
Molecular Weight:175.19

3,4-Pyridinediamine,N4-cyclopropyl-(9CI)

146950-68-7
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$157.00/250mg

530-62-1 Synthesis

530-62-1
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$6.00/25g

1-Cyclopropyl-1,3-dihydroimidazo[4,5-c]pyridine-2-one

380605-29-8
52 suppliers
$137.00/100mg

Yield:380605-29-8 78.2%

Reaction Conditions:

in acetonitrile at 0 - 20; for 16 h;

Steps:

1

The synthesis of l-(cyclopropyl)-l,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one (fragment CI) was done as shown in scheme 7.g 7 fragment C1; Scheme 7A round-bottom flask was charged with 3-nitro-4-chloropyridine (600 g, 3.8 mol), absolute EtOH (3L), diisopropylethylamine (DIPEA) (1320 mL, 7.6 mol) and cyclopropyl amine (432g, 7.6 mol). The resulting solution was refluxed for lOh. The reaction was cooled to 0°C, and the solid was collected by filtration. The filter cake was washed with cold ethanol (2x500 mL) to give compound 6. The mother liquor was concentrated and partitioned between water (1000 mL) and ethyl acetate (1000 mL). The aqueous layer was extracted with ethyl acetate (2x500mL), dried over MgS0₄, filtered, and concentrated to give a second batch of product (total: 650 g, 96%). A suspension of compound 6 (650g, 3.65mol) and 10% Pd/C (50% water; 163 g) in EtOH (7 L) was hydrogenated at 50 psi H₂ for 16 h at room temperature. The suspension was filtered through Celite and concentrated. The residue was dried in vacuo to provide compound 7 (490 g, 90.6%). To a solution of compound 7 (490 g, 3.29 mol) in CH₃CN (4 L) at 0°C was added carbonyldiimidazole (CDI) (559 g, 3.45 mol, 1.05eq.), and the resulting mixture was warmed to room temperature and stirred for 16 h at room temperature. The precipitate was collected by filtration and the solid was washed with cold CH₃CN (2 X 1000 mL). The solid was dried in vacuo to give fragment CI . (450 g, 78.2%). m/z = 176 (M+H). 1H NMR (400 MHz, DMSO-d₆) δ ppm 0.84 - 0.91 (m, 2 H), 0.98 - 1.06 (m, 2 H), 2.89 (tt, J=7.0, 3.5 Hz, 1 H), 7.18 (d, J=5.5 Hz, 1 H), 8.16 (s, 1 H), 8.19 (d, J=5.5 Hz, 1 H), 10.98 (br. s., 1 H).

References:

WO2012/80446,2012,A1 Location in patent:Page/Page column 18

31872-62-5 Synthesis