Water → HCID 57404565, compound

HRID 870286Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[CH:7]2[C:12]1[N:17]=[C:16]([O:18][CH3:19])[N:15]=[C:14]([CH3:20])[N:13]=1.CN1C=CN=C1.[F:27][CH:28]([F:33])[S:29](Cl)(=[O:31])=[O:30].O>ClCCl>[F:27][CH:28]([F:33])[S:29]([N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[F:1])[CH:7]([C:12]2[N:17]=[C:16]([O:18][CH3:19])[N:15]=[C:14]([CH3:20])[N:13]=2)[C:8]1=[O:11])(=[O:31])=[O:30]

Participants

Conditions

Temperature: 0 °C

Procedure

7-Fluoro-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-1,3-dihydro-2H-indol-2-one (1.20 g) and 1-methyl-1H-imidazole (0.97 g) are introduced as initial charge in 10 ml of dichloromethane and cooled to 0° C. under nitrogen. With stirring, difluoromethanesulfonyl chloride (1.21 g) is added in 2 portions and the mixture is warmed to room temperature. After 5 hours, 1-methyl-1H-imidazole (0.32 g) and difluoromethanesulfonyl chloride (0.61 g) are added and the mixture is stirred for 16 hours. After adding water and some hydrochloric acid, the solid is filtered off, washed with dichloromethane and water and dried. This gives the title compound as a solid in an HPLC purity of 91% (1.54 g, 92% of theory). The UV absorption (maximum at 360 nm) verifies the N-sulfonylation of the product.

Workup

temperaturethe mixture is warmed to room temperature
stirringthe mixture is stirred for 16 hours
filtrationsome hydrochloric acid, the solid is filtered off
washwashed with dichloromethane and water
customdried

Sources & evidence

ORD record: ord-be3e47d2f4dc4fa6ab98093614bbef3b
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969553B2

Reaction notes

Loading…