Hydrochloric Acid → HCID 178464667, Verbindung

HRID 1044715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1044715
Cl.[CH2:2]([NH:4][C:5]([N:7]1[CH2:11][C:10]([CH3:13])([CH3:12])[CH:9]=[N:8]1)=[NH:6])[CH3:3].CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.[Br:32][C:33]1[CH:34]=[C:35]([S:46](Cl)(=[O:48])=[O:47])[CH:36]=[CH:37][C:38]=1[NH:39][C:40](=[O:45])[C:41]([F:44])([F:43])[F:42].Cl>C1COCC1>[Br:32][C:33]1[CH:34]=[C:35]([S:46](=[O:48])(=[O:47])[N:6]=[C:5]([N:7]2[CH2:11][C:10]([CH3:12])([CH3:13])[CH:9]=[N:8]2)[NH:4][CH2:2][CH3:3])[CH:36]=[CH:37][C:38]=1[NH:39][C:40](=[O:45])[C:41]([F:43])([F:44])[F:42]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 581587063-Bromo-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chlorideHCID 178464603HCID 178464603, Verbindung

Produkt 1

HCID 178464667HCID 178464667, VerbindungAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1.20 g N-ethyl-4,4-dimethyl-4,5-dihydro-pyrazole-1-carboxamidine hydrochloride in 35 mL dry THF was added 5.1 mL (3.0 equiv.) BEMP and the reaction mixture was stirred for 10 minutes at room temperature. 2.15 g (1.0 equiv.) 3-Bromo-4-(2,2,2-trifluoro-acetylamino)-benzenesulfonyl chloride was added in one portion and the resulting bright yellow solution was stirred overnight at room temperature. The reaction mixture was acidified with 1N HCl and extracted twice with EA. The combined organic layers were dried over Na2SO4, filtered and evaporated under reduced pressure. Purification by flash chromatography (Et2O/PA 1:1→Et2O) afforded 2.29 g (78%) of product. 1H NMR (400 MHz, CDCl3) δ 1.18 (t, J=7.3 Hz, 3H), 1.24 (s, 6H), 3.43-3.51 (m, 2H), 3.79 (br.s, 2H), 6.78 (s, 1H), 7.93 (dd, J=8.6, 2.0 Hz, 1H), 8.19 (d, J=2.0 Hz, 1H), 8.39 (d, J=8.6 Hz, 1H), 8.61 (br.s., 1H).

Aufarbeitung

  1. stirringthe resulting bright yellow solution was stirred overnight at room temperature
  2. extractionextracted twice with EA
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customPurification by flash chromatography (Et2O/PA 1:1→Et2O)

Quellen und Nachweise

ORD-Eintrag
ord-6502296579454a179c9a8d521ec61f53
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563723B2

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