Methanol → 5-[5-(1-Azetidinylmethyl)-3-thienyl]-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide

3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide (105 mg, 0.26 mmol) was diluted in dimethylsulfoxide (0.5 mL) and methanol (0.5 mL) in a 2 dram vial. Azetidine (75 mg, 5 eq) was added, followed by glacial acetic acid (0.3 mL). The mixture was stirred at rt for 1 h, then sodium cyanoborohydride (35 mg, 0.56 mmol, 2.1 eq) was added and the mixture was stirred at rt overnight. The mixture was filtered through a 1 g silica gel pad (commercial, in syringe tube), and the solvent was removed in vacuo. The crude product was re-diluted in a mixture of methanol and DMSO, and purified by ammonium hydroxide Gilson HPLC. The desired fractions were concentrated in an EZ2 Genevac evaporator, giving 10 mg (9%) of title compound.

1. stirringthe mixture was stirred at rt overnight
2. filtrationThe mixture was filtered through a 1 g silica gel pad (commercial, in syringe tube)
3. customthe solvent was removed in vacuo
4. additionThe crude product was re-diluted in a mixture of methanol and DMSO
5. custompurified by ammonium hydroxide Gilson HPLC
6. concentrationThe desired fractions were concentrated in an EZ2 Genevac evaporator

ORDレコード

ord-fc64df5ec2cc491ca6491bd241a4d245

出典データセット

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08071584B2