Hydrochloric Acid → 3-(4,6-diethoxy-1,3,5-triazin-2-yl)-1-[(difluoromethyl)sulfonyl]-7-fluoro-1,3-dihydro-2H-indol-2-one

HRID 870289Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870289
[CH2:1]([O:3][C:4]1[N:9]=[C:8]([O:10][CH2:11][CH3:12])[N:7]=[C:6]([CH:13]2[C:21]3[C:16](=[C:17]([F:22])[CH:18]=[CH:19][CH:20]=3)[NH:15][C:14]2=[O:23])[N:5]=1)[CH3:2].CN1C=CN=C1.[F:30][CH:31]([F:36])[S:32](Cl)(=[O:34])=[O:33].Cl>ClCCl.O>[CH2:11]([O:10][C:8]1[N:9]=[C:4]([O:3][CH2:1][CH3:2])[N:5]=[C:6]([CH:13]2[C:21]3[C:16](=[C:17]([F:22])[CH:18]=[CH:19][CH:20]=3)[N:15]([S:32]([CH:31]([F:36])[F:30])(=[O:34])=[O:33])[C:14]2=[O:23])[N:7]=1)[CH3:12]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 13901-Methylimidazole2×HCID 73932Difluoromethanesulphonyl chloride2×HCID 679826823-(4,6-diethoxy-1,3,5-triazin-2-yl)-7-fluoro-1,3-dihydro-2H-indol-2-one

Produkt 1

HCID 574045673-(4,6-diethoxy-1,3,5-triazin-2-yl)-1-[(difluoromethyl)sulfonyl]-7-fluoro-1,3-dihydro-2H-indol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-(4,6-Diethoxy-1,3,5-triazin-2-yl)-7-fluoro-1,3-dihydro-2H-indol-2-one (1.0 g) and 1-methyl-1H-imidazole (0.51 g) are introduced as initial charge in 10 ml of dichloromethane and cooled to 0° C. under nitrogen. With stirring, difluoromethanesulfonyl chloride (0.46 g) is added dropwise and the mixture is after-stirred for 2 hours at 0° C. to 6° C. After adding 1-methyl-1H-imidazole (0.25 g) and difluoromethanesulfonyl chloride (0.23 g), the mixture is stirred for 2 hours at 0° C. to 10° C. After adding 5 ml of water, the mixture is adjusted to pH 2 using 10% strength hydrochloric acid, the organic solvent is largely distilled off in vacuo, and the solid is filtered off, washed with water and heptane and dried. This gives the title compound as a solid in an HPLC purity of 93% (1.19 g, 83% of theory). The UV absorption (maximum at 360 nm) verifies the N-sulfonylation of the product.

Aufarbeitung

  1. stirringthe mixture is after-stirred for 2 hours at 0° C. to 6° C
  2. stirringthe mixture is stirred for 2 hours at 0° C. to 10° C
  3. distillationthe organic solvent is largely distilled off in vacuo
  4. filtrationthe solid is filtered off
  5. washwashed with water and heptane
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5be7b2e09d654eb7bdac856355f569d2
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969553B2

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