Benzenesulfonyl chloride → N-[2-({[(1R)-1-Phenylethyl]amino}methyl)-3,4-dihydro-2H-chromen-7-yl]-2,1,3-benzoxadiazole-4-sulfonamide

HRID 49463

Reaktionsgleichung

[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:12]O)[O:9]2)=[CH:4][CH:3]=1.[N:14]1[O:15][N:16]=[C:17]2[C:22]([S:23](Cl)(=[O:25])=[O:24])=[CH:21][CH:20]=[CH:19][C:18]=12.C1(S(Cl)(=O)=O)C=CC=CC=1.[C:37]1([C@H:43]([NH2:45])[CH3:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>N1C=CC=CC=1.O>[C:37]1([C@H:43]([NH:45][CH2:12][CH:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][C:2]([NH:1][S:23]([C:22]4[C:17]5[C:18](=[N:14][O:15][N:16]=5)[CH:19]=[CH:20][CH:21]=4)(=[O:25])=[O:24])=[CH:3][CH:4]=3)[O:9]2)[CH3:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A solution of (7-amino-3,4-dihydro-2H-chromen-2-yl)methanol (28.6 mg, 160 μmol) in pyridine is treated with 2,1,3-benzoxadiazole-4-sulfonyl chloride (39 mg, 180 μmol) at ambient temperatures, stirred for 1 h, treated with phenylsulfonyl chloride (23 μL, 180 μmol) stirred for an additional hour at ambient temperatures, treated with (1R)-1-phenyl-1-ethanamine (1.6 mmol, 206 μL), heated to 100° C. for 2 h, cooled to room temperature, diluted with water and extracted with ethyl acetate. The extracts are combined, dried over Na2SO4 and concentrated in vacuo. The resultant residue is purified by reverse phase preparative HPLC to give the title product, M+H 465, retention time 3.89 min.

Aufarbeitung

stirringstirred for an additional hour at ambient temperatures
temperaturecooled to room temperature
extractionextracted with ethyl acetate
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe resultant residue is purified by reverse phase preparative HPLC

Quellen und Nachweise

ORD-Eintrag: ord-4be1e33e70914c3a85aad06d6d29f8d9
Quelldatensatz: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06706757B2

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