Diisopropylethylamine → (1-{4-[Methyl-(tetrahydro-pyran-4-carbonyl)-amino]-benzenesulfonyl}-piperidin-4-yl)-carbamic acid tert-butyl ester

HRID 337212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 337212
[C:1]([O:5][C:6](=[O:25])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][CH3:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[O:35]1[CH2:40][CH2:39][CH:38]([C:41](Cl)=[O:42])[CH2:37][CH2:36]1>C1COCC1>[C:1]([O:5][C:6](=[O:25])[NH:7][CH:8]1[CH2:9][CH2:10][N:11]([S:14]([C:17]2[CH:18]=[CH:19][C:20]([N:23]([CH3:24])[C:41]([CH:38]3[CH2:39][CH2:40][O:35][CH2:36][CH2:37]3)=[O:42])=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH2:12][CH2:13]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2795505Oxane-4-carbonyl chlorideHCID 71060136[1-(4-Methylamino-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

Produkt 1

HCID 71060228(1-{4-[Methyl-(tetrahydro-pyran-4-carbonyl)-amino]-benzenesulfonyl}-piperidin-4-yl)-carbamic acid tert-butyl esterAusbeute 100,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

[1-(4-Methylamino-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (0.13 g, 0.35 mmol) was dissolved in THF (5 ml). To this was added diisopropylethylamine (0.18 ml, 0.7 mmol) in one portion followed by the drop wise addition of tetrahydro-2H-pyran-4-carbonyl chloride (0.06 ml, 0.38 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. After this time the mixture was concentrated, diluted with DCM (200 ml) and washed sequentially with HCl (1M solution, 10 ml), NaOH (1M solution, 10 ml) and brine (10 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated to give the title compound (0.17 g, 98% yield) as a white powder which was taken on without further purification. Tr=1.89 min m/z (ES+) (M+Na+) 504.

Aufarbeitung

  1. concentrationAfter this time the mixture was concentrated
  2. additiondiluted with DCM (200 ml)
  3. washwashed sequentially with HCl (1M solution, 10 ml), NaOH (1M solution, 10 ml) and brine (10 ml)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-53cebd2059fb423499af9799a08148ee
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889716B2

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