Diisopropylethylamine → HCID 89726475, Verbindung

HRID 1777728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1777728
Br[C:2]1[S:6][CH:5]=[N:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].[C:11]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][C@H:19]1[CH3:24])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].CCN(C(C)C)C(C)C>CN1C(=O)CCC1.CC(=O)OCC>[C:14]([O:13][C:11]([N:18]1[CH2:23][CH2:22][N:21]([C:2]2[S:6][CH:5]=[N:4][C:3]=2[C:7]([O:9][CH3:10])=[O:8])[CH2:20][C@H:19]1[CH3:24])=[O:12])([CH3:17])([CH3:15])[CH3:16]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 10262201tert-Butyl (2R)-2-methylpiperazine-1-carboxylateHCID 40787018Methyl 5-bromo-1,3-thiazole-4-carboxylate

Produkt 1

HCID 89726475HCID 89726475, VerbindungAusbeute 30,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of methyl 5-bromo-1,3-thiazole-4-carboxylate (3 g) in NMP (30 mL) was added (R)-1-N-Boc-2-methylpiperazine (2.76 g) followed by DIPEA (10.1 mL). The resulting solution was stirred at 120° C. for 1.5 d, at RT over weekend and at 120° C. for 7 h. After cooling down, the reaction mixture was diluted with EA and washed with sat. aq. NaHCO3, 1M HCl and sat. aq NaCl. The aq. phases were extracted with EA. The combined org. layers were dried over Na2SO4, filtrated off and evaporated in vacuo. The crude was purified by CC (Biotage, SNAP 100 g cartridge, solvent A: Hept; solvent B: EA; gradient in % B: 0 for 10CV, 0 to 10 over 5CV, 10 for 5CV, 10 to 20 over 5CV, 20 for 5CV, 20 to 30 over 5CV, 30 for 5CV) to afford 1.42 g of yellow oil. LC-MS (B): tR=0.84 min; [M+H]+: 342.08.

Aufarbeitung

  1. temperatureAfter cooling down
  2. washwashed with sat. aq. NaHCO3, 1M HCl and sat. aq NaCl
  3. extractionThe aq. phases were extracted with EA
  4. dry with materiallayers were dried over Na2SO4
  5. filtrationfiltrated off
  6. customevaporated in vacuo
  7. customThe crude was purified by CC (Biotage, SNAP 100 g cartridge, solvent A: Hept; solvent B: EA; gradient in % B: 0 for 10CV, 0 to 10 over 5CV, 10 for 5CV, 10 to 20 over 5CV, 20 for 5CV, 20 to 30 over 5CV, 30 for 5CV)

Quellen und Nachweise

ORD-Eintrag
ord-076e2cae0c914f1b89abd6e200a6f4b8
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266876B2

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