Reaktion #966790

ord-90157d1c5d49420a9e540ea3642735d4

Reaktionsgleichung

COC(=O)[C@@H](OC(C)(C)C)c1c(C)cc2nc(-c3ccnc(Cl)n3)sc2c1-c1ccc(Cl)cc1
(S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate
C[C@@H]1CNCCN1C(=O)OC(C)(C)C
(R)-1-boc-2-methylpiperazine
CCN(CC)CC
triethylamine
COC(=O)[C@@H](OC(C)(C)C)c1c(C)cc2nc(-c3ccnc(N4CCN(C(=O)OC(C)(C)C)[C@H](C)C4)n3)sc2c1-c1ccc(Cl)cc1
(R)-tert-butyl 4-(4-(6-((S)-1-tert-butoxy-2-methoxy-2-oxoethyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-2-yl)pyrimidin-2-yl)-2-methylpiperazine-1-carboxylate

Lösungsmittel

Reaktionsbedingungen

Temperatur
40°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.WAITat 40° C. for an additional 7 h
  2. 2
    FiltrationThe reaction mixture was filtered through Celite (ethyl acetate eluent)
  3. 3
    Einengenconcentrated
  4. 4
    Sonstigeused without further purification

Vorschrift

To (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (80.0 mg, 0.155 mmol) and (R)-1-boc-2-methylpiperazine (93.1 mg, 0.465 mmol) in 1,4-dioxane (2 mL) was added triethylamine (156.8 mg, 0.19 mL, 1.549 mmol). The reaction mixture was stirred at 40° C. for 4 h, at room temperature overnight, then at 40° C. for an additional 7 h. The reaction mixture was filtered through Celite (ethyl acetate eluent), concentrated, and used without further purification. LCMS-ESI+ calc'd for C35H43ClN5O5S (M+H+): 680.3; Found: 680.0 (M+H+).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08987250B2uspto-grants-2015_03