tert-Butyl piperazine-1-carboxylate → tert-Butyl-4-(2-{[2,5-bis(trifluoromethyl)benzyl]sulfonyl}thieno[3,2-c]pyridin-4-yl)piperazine-1-carboxylate

HRID 549296

Reaktionsgleichung

Reaktionsgleichung von HRID 549296
Cl[C:2]1[C:7]2[CH:8]=[C:9]([S:11]([O-:13])=[O:12])[S:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[Li+].[F:15][C:16]([F:30])([F:29])[C:17]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:18]=1[CH2:19]Br.[C:31]([O:35][C:36]([N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)=[O:37])([CH3:34])([CH3:33])[CH3:32]>C(#N)C>[C:31]([O:35][C:36]([N:38]1[CH2:43][CH2:42][N:41]([C:2]2[C:7]3[CH:8]=[C:9]([S:11]([CH2:19][C:18]4[CH:21]=[C:22]([C:25]([F:28])([F:27])[F:26])[CH:23]=[CH:24][C:17]=4[C:16]([F:30])([F:29])[F:15])(=[O:13])=[O:12])[S:10][C:6]=3[CH:5]=[CH:4][N:3]=2)[CH2:40][CH2:39]1)=[O:37])([CH3:34])([CH3:32])[CH3:33]

Komponenten

5

Edukt 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27731992-(Bromomethyl)-1,4-bis(trifluoromethyl)benzeneHCID 86591057Lithium 4-chlorothieno[3,2-c]pyridine-2-sulfinate

Produkt 1

HCID 86591058tert-Butyl-4-(2-{[2,5-bis(trifluoromethyl)benzyl]sulfonyl}thieno[3,2-c]pyridin-4-yl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Lithium 4-chlorothieno[3,2-c]pyridine-2-sulfinate (0.44 mmol) was treated with 2,5-bis(trifluoromethyl)benzylbromide (0.59 mmol) as described in Method P above and then reacted further with tert-butyl-piperazine-1-carboxylate as described in Method Q. Yield 0.01 g (4% over two steps). Beige solid. 1H NMR (300 MHz, CDCl3) δ 8.16 (d, J=5.8 Hz 1H), 8.00 (s, 1H), 7.74-7.85 (m, 3H), 4.76 (s, 2H), 3.56-3.64 (m, 4H), 3.47-3.56 (m, 4H), 1.49 (s, 9H); MS (ESI+) for C25H25F6N3O4S2 m/z 610 (M+H)+. HPLC 73%, RT 2.36 min (YMC ODS AQ, 33×3 mm, 10-90% acetonitrile in 3 min).

Quellen und Nachweise

ORD-Eintrag
ord-217fe29634db4e829e290e8ae1cd0930
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943639B2

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