Triethylamine → 2-(4-Fluoro-phenyl)-7,10-bis-methanesulfonyl-5-methylene-5,6,7,8,9,10-hexahydro-1-oxa-7,10,11-triaza-cycloocta[f]indene-3-carboxylic acid methylamide

HRID 2190185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2190185
[CH3:1][NH:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]3[C:14](=[CH2:24])[CH2:15][NH:16][CH2:17][CH2:18][N:19]([S:20]([CH3:23])(=[O:22])=[O:21])[C:10]3=[N:9][C:8]=2[O:7][C:6]=1[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)=[O:4].[CH3:32][S:33](Cl)(=[O:35])=[O:34].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][NH:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]3[C:14](=[CH2:24])[CH2:15][N:16]([S:33]([CH3:32])(=[O:35])=[O:34])[CH2:17][CH2:18][N:19]([S:20]([CH3:23])(=[O:22])=[O:21])[C:10]3=[N:9][C:8]=2[O:7][C:6]=1[C:25]1[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=1)=[O:4]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 666644732-(4-Fluoro-phenyl)-10-methanesulfonyl-5-methylene-5,6,7,8,9,10-hexahydro-1-oxa-7,10,11-triaza-cycloocta[f]indene-3-carboxylic acid methylamide

Produkt 1

HCID 666642522-(4-Fluoro-phenyl)-7,10-bis-methanesulfonyl-5-methylene-5,6,7,8,9,10-hexahydro-1-oxa-7,10,11-triaza-cycloocta[f]indene-3-carboxylic acid methylamideAusbeute 44,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-(4-Fluoro-phenyl)-10-methanesulfonyl-5-methylene-5,6,7,8,9,10-hexahydro-1-oxa-7,10,11-triaza-cycloocta[f]indene-3-carboxylic acid methylamide (6.0 mg, 0.013 mmol) is dissolved in DCM (2 mL) and the solution is cooled to 0° C. Methanesulfonyl chloride (7.7 mg, 0.07 mmol) is added followed by triethylamine (6.83 mg, 0.07 mmol) and the reaction is allowed to warm up to RT over 3 h then evaporated to dryness and placed on the high vacuum overnight. The sample is then redissolved in EtOAc (25 mL) and then washed with 1N HCl (10 mL), then Brine (20 mL) and dried over Na2SO4. The organic is concentrated to afford 2-(4-Fluoro-phenyl)-7,10-bis-methanesulfonyl-5-methylene-5,6,7,8,9,10-hexahydro-1-oxa-7,10,11-triaza-cycloocta[f]indene-3-carboxylic acid methylamide (3 mg, 42%). MS-ES [M+H]+=523.0.

Aufarbeitung

  1. temperatureto warm up to RT over 3 h
  2. customthen evaporated to dryness
  3. customplaced on the high vacuum overnight
  4. dissolutionThe sample is then redissolved in EtOAc (25 mL)
  5. washwashed with 1N HCl (10 mL)
  6. dry with materialBrine (20 mL) and dried over Na2SO4
  7. concentrationThe organic is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-825c9085c554484d81cb3c266e732492
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324239B2

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