Phosphorus trichloride → HCID 135497089, compound

To a suspension of 1-[(6-chloro-1-oxidopyridin-3-yl)methyl]-4-methylpiperazine (0.145 g, 0.60 mmol) and 2-oxoindoline-6-carbonitrile (0.100 g, 0.63 mmol) in tetrahydrofuran (3 mL), was added sodium bis(trimethylsilyl)amide (1.4 mL, 1.4 mmol). The mixture was stirred for 5 min at room temperature and then heated in a microwave oven at 110° C. for 10 min. The mixture was quenched with methanol (2 mL) followed by evaporation to dryness. The dry product mixture was dissolved in ethyl acetate/acetonitrile, (1:1, 5 mL), is and phosphorus trichloride (0.5 mL, 5.73 mmol) was added. The mixture was stirred at 60° C. for 3 h and then concentrated in vacuo. The residue was purified on a silica gel column using a gradient dichloromethane/methanol, (100:1 to 2:1), as the eluent. The resulting yellow solid was dissolved in dichloromethane/methanol, (9:1), and treated with HCl in diethyl ether (1 M) at 0° C. The resulting yellow crystals were collected by filtration and washed with diethyl ether to obtain 0.025 g (9% yield) of the title compound: MS (ESP) m/z 348 (M++1).

1. temperatureheated in a microwave oven at 110° C. for 10 min
2. customThe mixture was quenched with methanol (2 mL)
3. customfollowed by evaporation to dryness
4. dissolutionThe dry product mixture was dissolved in ethyl acetate/acetonitrile, (1:1, 5 mL),
5. stirringThe mixture was stirred at 60° C. for 3 h
6. concentrationconcentrated in vacuo
7. customThe residue was purified on a silica gel column
8. dissolutionThe resulting yellow solid was dissolved in dichloromethane/methanol, (9:1),
9. additiontreated with HCl in diethyl ether (1 M) at 0° C
10. filtrationThe resulting yellow crystals were collected by filtration
11. washwashed with diethyl ether

ORD record

ord-3a94561bd93145a4a91e33cedd2cd652

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07683067B2