Diisopropylethylamine → n-((Dimethylamino)acetyl)-1-methyl-n-(3,4,5-trimethoxyphenyl)-1h-indole-5-sulfonamide

Temperature

0 °C

A solution of Example 4 (20.0 g, 53.2 mmol) in THF (250 mL) at room temperature was treated with dimethylaminoacetyl chloride hydrochloride (12.3 g, 77.8 mmol), DMAP (650 mg, 5.3 mmol), and diisopropylethylamine (25.2 g, 195.0 mmol), stirred for 8 hours, and concentrated to ⅓ its original volume. The mixture was diluted with ethyl acetate (400 mL), washed with 5% NaHCO3 (2×200 mL) and water (200 mL), dried (Na2SO4), filtered, concentrated to a volume of 120 mL, diluted with methyl tert-butyl ether (120 mL), stirred for 18 hours, cooled to 0° C., stirred for 2 hours, and filtered. The resulting solid was washed with 1:1 ethyl acetate/methyl tert-butyl ether (100 mL) and dried under vacuum to provide 22.5 g (92%) of the desired product.

1. concentrationconcentrated
2. additionThe mixture was diluted with ethyl acetate (400 mL)
3. washwashed with 5% NaHCO3 (2×200 mL) and water (200 mL)
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated to a volume of 120 mL
7. additiondiluted with methyl tert-butyl ether (120 mL)
8. stirringstirred for 18 hours
9. stirringstirred for 2 hours
10. filtrationfiltered
11. washThe resulting solid was washed with 1:1 ethyl acetate/methyl tert-butyl ether (100 mL)
12. customdried under vacuum

ORD record

ord-00d084a0718e4d45adc6d05b8ef4d1b0

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06710185B2