Triethylamine → 3-[2-((R)-sec-Butylamino)-3,4-dioxo-cyclobut-1-enylamino]-6-chloro-N-ethyl-2-hydroxy-N-methoxy-benzenesulfonamide

HRID 1669602

Reaktionsgleichung

Reaktionsgleichung von HRID 1669602
[Cl:1][C:2]1[C:7]([S:8]([N:11]([O:14][CH3:15])[CH2:12][CH3:13])(=[O:10])=[O:9])=[C:6]([OH:16])[C:5]([NH:17][C:18]2[C:21](=O)[C:20](=[O:23])[C:19]=2[O:24]CC)=[CH:4][CH:3]=1.[NH2:27][C@@H:28]([CH2:30][CH3:31])[CH3:29].C(N(CC)CC)C>CC#N.CCO>[C@H:28]([NH:27][C:21]1[C:20](=[O:23])[C:19](=[O:24])[C:18]=1[NH:17][C:5]1[C:6]([OH:16])=[C:7]([S:8]([N:11]([CH2:12][CH3:13])[O:14][CH3:15])(=[O:10])=[O:9])[C:2]([Cl:1])=[CH:3][CH:4]=1)([CH2:30][CH3:31])[CH3:29]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 2724537(R)-sec-butylamineHCID 866386316-Chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-ethyl-benzenesulfonamide

Produkt 1

HCID 446291483-[2-((R)-sec-Butylamino)-3,4-dioxo-cyclobut-1-enylamino]-6-chloro-N-ethyl-2-hydroxy-N-methoxy-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a stirred solution of 6-Chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-ethyl-benzenesulfonamide (Intermediate FA) (100 mg, 0.25 mmol) in MeCN (1 ml) and EtOH (1 ml) was added (R)-(−)-2-Aminobutane (30.7 mg, 0.42 mmol) followed by triethylamine (69 μl, 0.49 mmol). The reaction mixture was heated at 70° C. for 1 hour. The reaction mixture was concentrated in vacuo and dissolved in EtOAc. The EtOAc solution was washed with 1M HCl (aq) and concentrated in vacuo. The residue was triturated with DCM to give a white solid; [M+H]+ 432.2. 1H NMR (DMSO) 0.9 (3H, t, CH3), 1.2 (6H, m), 1.5-1.6 (2H, m), 3.3 (2H, m), 3.7 (3H, s, CH3) 4.1 (1H, m), 7.3 (1H, d), 8.1 (1H, d), 8.3 (1H, d), 9.4 (1H, s), 10.1 (1H, s).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in EtOAc
  3. washThe EtOAc solution was washed with 1M HCl (aq)
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with DCM
  6. customto give a white solid

Quellen und Nachweise

ORD-Eintrag
ord-94004b851df4424eb5f21dd651ae8d16
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989497B2

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