Benzenesulfonyl chloride → HCID 86760979, Verbindung

HRID 1432952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432952
[OH-].[Na+].[C:3]1([S:9](Cl)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:13]([O:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[NH:38][C:37]3[CH:36]=[CH:35][N:34]=[C:33]([Cl:39])[C:32]=3[CH:31]=2)[C:25](=[O:40])[CH2:24]1)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.C(Cl)Cl>[CH2:13]([O:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[N:38]([S:9]([C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)(=[O:11])=[O:10])[C:37]3[CH:36]=[CH:35][N:34]=[C:33]([Cl:39])[C:32]=3[CH:31]=2)[C:25](=[O:40])[CH2:24]1)=[O:22])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

6

Edukt 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 53757606Phenylmethyl 4-[(4-chloro-1H-pyrrolo[3,2-c]pyridin-2-yl)methyl]-3-oxo-1-piperazinecarboxylate

Produkt 1

HCID 86760979HCID 86760979, VerbindungAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Powdered NaOH (0.96 g, 23.9 mmol) followed by nBu4NHSO4 (0.32 g, 0.96 mmol) and benzene sulfonyl chloride (1.8 mL, 14.1 mmol) is added to a solution of 4-(4-chloro-1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-3-oxo-piperazine-1-carboxylic acid benzyl ester (3.81 g, 9.56 mmol) in CH2Cl2(32 mL) at RT. The resulting slurry is stirred for 3.5 h then diluted with CH2Cl2 and washed with saturated NaHCO3 and brine. The organic layer is dried over MgSO4, filtered and concentrated to dryness. The crude product is chromatographed eluting with 1-5% MeOH/CH2Cl2 to yield the title product (5.06 g, 9.38 mmol). 1H NMR (CDCl3, 300 MHz) δ8.23 (d, 1H), 7.97 (d, 1H), 7.84 (d, 2H), 7.61 (d, 1H), 7.51 (m, 2H), 7.38 (s, 5H), 6.50 (s, 1H), 5.18 (s, 2H), 5.03 (s, 2H), 4.29 (s, 2H), 4.29 (s, 2H), 3.80 (m, 2H), 3.51 (m, 2H). Ion spray [M+H]+=539, 541, Cl pattern.

Aufarbeitung

  1. washwashed with saturated NaHCO3 and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe crude product is chromatographed
  6. washeluting with 1-5% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-5ebdf93f370b4244ac2be3ab1a28ed16
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612075B2

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